Table 4.

The physicochemical properties of intermediates 4–18

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