Carbon Tetrachloride → 1-(Chloromethyl)-3,5-bis(trifluoromethyl)benzene

HRID 962950

Reaction equation

HRID 962950 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:20][C:21]([F:35])([F:34])[C:22]1[CH:23]=[C:24]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[CH2:25]O.CCCCC.C(Cl)(Cl)(Cl)[Cl:42]>>[F:20][C:21]([F:35])([F:34])[C:22]1[CH:23]=[C:24]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[CH2:25][Cl:42]

Participants

5

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8003PentaneHCID 11776TriphenylphosphineHCID 1229333,5-Bis(trifluoromethyl)benzyl alcohol

Product 1

HCID 1235761-(Chloromethyl)-3,5-bis(trifluoromethyl)benzeneYield 59%

Procedure

Triphenylphosphine (371 mg, 1.41 mmol) was added to a solution of 3,5-bistrifluoromethylbenzyl alcohol (257 mg, 1.05 mmol) in dry CCl4 (2 ml). The mixture was refluxed for 1 h, then cooled to room temp. Pentane (2 ml) was added, and the mixture stirred for a further 5 min., then filtered. The solid was washed with pentane (2 ml), and the filtrate concentrated in vacuo. The crude product was purified by column chromatography [SiO2: hexane-ethyl acetate 4:1] to give 3,5-bistrifluoromethylbenzyl chloride (162 mg, 59%); TLC (hexane-ethyl acetate 1:1) rf=0.73.

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. filtrationfiltered
  3. washThe solid was washed with pentane (2 ml)
  4. concentrationthe filtrate concentrated in vacuo
  5. customThe crude product was purified by column chromatography [SiO2: hexane-ethyl acetate 4:1]

Sources & evidence

ORD record
ord-91e2fcaf04b64c868c7f232e5e96d6f5
Source dataset
uspto-grants-1998_06
Patent number
US05760248

Linked notes

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