Water → 7-Benzyloxy-2,2-dimethyl-4-(4-trifluoromethylphenyl)-2H-chromene

HRID 26287Notes

Reaction equation

HRID 26287 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1.[CH2:17]([O:24][C:25]1[CH:34]=[C:33]2[C:28]([C:29](=O)[CH2:30][C:31]([CH3:36])([CH3:35])[O:32]2)=[CH:27][CH:26]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>CCOCC>[CH2:17]([O:24][C:25]1[CH:34]=[C:33]2[C:28]([C:29]([C:7]3[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=3)=[CH:30][C:31]([CH3:36])([CH3:35])[O:32]2)=[CH:27][CH:26]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 156096367-Benzyloxy-2,3-dihydro-2,2-dimethyl-4-oxobenzopyranHCID 178418339Butyllithium

Product 1

HCID 205705607-Benzyloxy-2,2-dimethyl-4-(4-trifluoromethylphenyl)-2H-chromeneYield 90.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

n-Butyl-lithium (142 ml of a 2.4 M solution) was added under dry nitrogen to a solution of 4-bromobenzotrifluoride (76.5 g) in dry ether at -50° C. The mixture was left to stir for 2 hours. 7-Benzyloxy-2,2-dimethylchroman-4-one (64 g) in dry ether was added dropwise. Water was added and the ether layer washed with 5 N.HCl (2×100 ml), and dried (MgSO4). Removal of the solvent under reduced pressure gave an oil (84 g) which was chromatographed on alumina. Elution with petrolether (1:1) gave the title compound (52 g).

Workup

  1. waitThe mixture was left
  2. washthe ether layer washed with 5 N
  3. dry with materialHCl (2×100 ml), and dried (MgSO4)
  4. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-010863142bda486a8cf17ced1ff2d67f
Source dataset
uspto-grants-1979_04
Patent number
US04148909

Reaction notes

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