Benzene, 1-bromo-3-(trifluoromethyl)- → 2,2-Dimethyl-4-(3-trifluoromethylphenyl)-2H-chromene-7-ol

Participants

Role	Name	HCID	Charge
Reactant	Benzene, 1-bromo-3-(trifluoromethyl)-	HCID 9817	—
Reactant	Ammonium Chloride	HCID 25517	—
Reactant	7-hydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-one	HCID 600902	—
Reactant	Magnesium	HCID 5462224	—
Solvent	Diethyl Ether	HCID 3283	—
Product	2,2-Dimethyl-4-(3-trifluoromethylphenyl)-2H-chromene-7-ol	HCID 12071757	86.2%

Reaction Steps

3-Bromobenzotrifluoride (61 g) in dry ether (100 ml was added to magnesium (6.6 g) in ether (50 ml). 2,2-Dimethylchroman-4-one-7-ol (17.4 g) suspended in ether (500 ml) was added and the mixture refluxed for 16 hourss. The reaction mixture was poured into ammonium chloride solution and extracted with ether. The combined ether layers were washed with 2N HCL (2×100 ml) and dried (MgSO4). Removal of the solvent under reduced pressure gave the title compound (25 g), m.p. 102°-106° C.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US04167515
Source dataset	uspto-grants-1979_09
ORD ID	ord-b10f98bb1e034bac837bc74d799c56f7
Source note	uspto-grants-1979_09