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Table 4 The physicochemical properties of intermediates 418

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