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

HRID 1863049Notes

Reaction equation

HRID 1863049 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:6][CH:7]=1.[Mg].[CH3:13][C:14]1([CH3:26])[CH2:23][C:22](=O)[C:21]2[C:16](=[CH:17][C:18]([OH:25])=[CH:19][CH:20]=2)[O:15]1.[Cl-].[NH4+]>CCOCC>[CH3:13][C:14]1([CH3:26])[CH:23]=[C:22]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:3]=2)[C:21]2[C:16](=[CH:17][C:18]([OH:25])=[CH:19][CH:20]=2)[O:15]1

Participants

6

Reactant 4

HCID 9817Benzene, 1-bromo-3-(trifluoromethyl)-HCID 25517Ammonium ChlorideHCID 6009027-hydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-oneHCID 5462224Magnesium

Product 1

HCID 120717572,2-Dimethyl-4-(3-trifluoromethylphenyl)-2H-chromene-7-olYield 86.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

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.

Workup

  1. additionwas added
  2. temperaturethe mixture refluxed for 16 hourss
  3. extractionextracted with ether
  4. washThe combined ether layers were washed with 2N HCL (2×100 ml)
  5. dry with materialdried (MgSO4)
  6. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-b10f98bb1e034bac837bc74d799c56f7
Source dataset
uspto-grants-1979_09
Patent number
US04167515

Reaction notes

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