Carbon tetrabromide → 2-(Trifluoromethoxy)benzyl bromide
Reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:34]>CCOCC>[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][Br:34]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 2-trifluoromethoxybenzyl alcohol (0.81 g, 4.5 mmol) from Step 1 above in ether (20 mL) at 0° C. was added triphenylphosphine (2.4 g, 9.2 mmol) and CBr4 (3.0 g, 9.2 mmol). The mixture was warmed to ambient temperature and stirred for 18 h. The ether was decanted from the gummy precipitate of triphenylphosphine oxide and evaporated under reduced pressure. The residue was purified by pressurized silica gel column chromatography using hexanes as eluant to give 2-trifluoromethoxybenzyl bromide as a colorless liquid (TLC Rf =0.80 (hexanes)).
Workup
- customThe ether was decanted from the gummy precipitate of triphenylphosphine oxide
- customevaporated under reduced pressure
- customThe residue was purified by pressurized silica gel column chromatography
Sources & evidence
- ORD record
- ord-c3a11549b53e4a82b4e72dacf1a4540b
- Source dataset
- uspto-grants-2000_07
- Patent number
- US06090805
Reaction notes
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