Carbon tetrabromide → 4-(Bromomethyl)-1-cyclohexyl-2-(trifluoromethyl)benzene

HRID 1828704

Reaction equation

HRID 1828704 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH2:13]O)=[CH:9][C:8]=2[C:15]([F:18])([F:17])[F:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Br)(Br)(Br)[Br:39]>C(Cl)Cl>[Br:39][CH2:13][C:10]1[CH:11]=[CH:12][C:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[C:8]([C:15]([F:18])([F:17])[F:16])[CH:9]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 22057748[4-Cyclohexyl-3-(trifluoromethyl)phenyl]methanol

Product 1

HCID 220577494-(Bromomethyl)-1-cyclohexyl-2-(trifluoromethyl)benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of (4-cyclohexyl-3-trifluoromethyl-phenyl)-methanol (300 mg, 1.16 mmol) and PPh3 (460 mg, 1.74 mmol) in DCM (5 mL) at 0° C. is added CBr4 (580 mg, 1.74 mmol) dissolved in DCM (2 mL). The reaction is stirred at 0° C. for 1 h followed by concentration. The residue obtained is purified by silica gel chromatography (5% EtOAc in hexanes) to give 4-bromomethyl-1-cyclohexyl-2-trifluoromethyl-benzene as a white solid.

Workup

  1. concentrationfollowed by concentration
  2. customThe residue obtained
  3. customis purified by silica gel chromatography (5% EtOAc in hexanes)

Sources & evidence

ORD record
ord-30e006357a934be687f5293472599046
Source dataset
uspto-grants-2006_06
Patent number
US07060697B2

Linked notes

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