Table 4 The physicochemical properties of intermediates 4–18
From: gem-Difluorobisarylic derivatives: design, synthesis and anti-inflammatory effect
Compound | IUPAC Name | Aspect | Mass of the starting material | Mass of the product | Rf value (PE:EtOAc) | m.p. (oC) | % yield |
|---|---|---|---|---|---|---|---|
4 | Methyl 4-(3-bromophenyl)-4-hydroxybut-2- ynoate | Yellow oil | 4 g | 3.9 g | 0.30 (8:2) | – | 70 |
5 | Methyl 4-(3-bromophenyl)-4-oxobut-2-ynoate | Yellow solid | 2.10 g | 1.59 g | 0.40 (9:1) | 102–104 | 80 |
6 | Methyl 2-(3-bromobenzoyl)-4,5-dimethylcyclohexa-1,4-dienecarboxylate | Yellow solid | 410 mg | 560 mg | 0.43 (9:1) | 100–102 | 96 |
7 | Methyl 2-(3-bromobenzoyl)-4,5-dimethylbenzoate | Yellow solid | 937 mg | 810 mg | 0.34 (9:1) | 122–124 | 87 |
8 | Methyl 4-(3-bromophenyl)-4,4-difluorobut-2-ynoate | Colorless oil | 350 mg | 270 mg | 0.44 (9:1) | – | 71 |
9 | Methyl 2-((3-bromophenyl)difluoromethyl)-4,5-dimethylcyclohexa-1,4-dienecarboxylate | White solid | 757 mg | 925 mg | 0.44 (9:1) | 72–74 | 95 |
10 | Methyl 2-((3-bromophenyl)difluoromethyl)-4,5-dimethylbenzoate | Yellow solid | 808 mg | 731 mg | 0.51 (9:1) | 60–62 | 91 |
11 | Methyl 4,5-dimethyl-2-(3-(prop-1-en-2-yl)benzoyl)benzoate | White solid | 782 mg | 640 mg | 0.34 (9:1) | 82–48 | 92 |
12 | Methyl 2-(difluoro(3-(prop-1-en-2-yl)phenyl)methyl)-4,5-dimethylbenzoate | Yellow oil | 640 mg | 539 mg | 0.35 (9:1) | – | 94 |
13 | Methyl 2-(3-(1-hydroxypropan-2-yl)benzoyl)-4,5-dimethylbenzoate | Yellow oil | 400 mg | 309 mg | 0.42 (7:3) | – | 73 |
14 | Methyl 2-(difluoro(3-(1-hydroxypropan-2-yl)phenyl)methyl)-4,5-dimethylbenzoate | Yellow oil | 240 mg | 192 mg | 0.36 (7.5:2.5) | – | 76 |
15 | (2-((3-bromophenyl)difluoromethyl)-4,5-dimethylphenyl)methanol | White solid | 100 mg | 88 mg | 0.26 (9:1) | 62–64 | 95 |
16 | (2-(difluoro(3-(prop-1-en-2-yl)phenyl)methyl)-4,5-dimethylphenyl)methanol | Yellow oil | 148 mg | 88 mg | 0.37 (8:2) | – | 65 |
17 | Methyl 2-(difluoro(3-isopropylphenyl)methyl)-4,5-dimethylbenzoate | White solid | 498 mg | 476 mg | 0.72 (9:1) | 116–118 | 95 |
18 | (2-(difluoro(3-isopropylphenyl)methyl)-4,5-dimethylphenyl)methanol | White solid | 294 mg | 260 mg | 0.69 (9:1) | 80–82 | 96 |