Water → 4-(Bromomethyl)-1-(cyclohexylmethyl)-2-(trifluoromethyl)benzene

HRID 2040557Notes

Reaction equation

HRID 2040557 reaction equation
[CH:1]1([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14]O)=[CH:10][C:9]=2[C:16]([F:19])([F:18])[F:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:20]P(Br)Br.O>C(Cl)Cl>[Br:20][CH2:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[C:9]([C:16]([F:19])([F:18])[F:17])[CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 67211680(4-(Cyclohexylmethyl)-3-(trifluoromethyl)phenyl)methanol

Product 1

HCID 672108914-(Bromomethyl)-1-(cyclohexylmethyl)-2-(trifluoromethyl)benzeneYield 198.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (4-(cyclohexylmethyl)-3-(trifluoromethyl)phenyl)methanol (80 mg, 0.29 mmol) in dry DCM (1 mL) was added tribromophosphine (11 μL, 0.12 mmol) at 0° C. The reaction mixture was slowly warmed to room temperature and stirred for 1 h, poured into water, extracted with DCM. The combined organics were washed with saturated NaHCO3 solution and brine, dried and concentrated. The residue was purified by column chromatography to give the title compound (80 mg) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 0.96-1.06 (m, 2H), 1.14-1.22 (m, 3H), 1.55-1.72 (m, 6H), 2.65 (d, J=6.5 Hz, 2H), 4.49 (s, 2H), 7.28 (d, J=8.0 Hz, 1H), 7.47 (dd, J=8.0 and 1.7 Hz, 1H), 7.63 (d, J=1.6 Hz, 1H).

Workup

  1. extractionextracted with DCM
  2. washThe combined organics were washed with saturated NaHCO3 solution and brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-778700b12ccc4b0e8d4d1d6408f016a5
Source dataset
uspto-grants-2013_11
Patent number
US08580841B2

Reaction notes

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