Carbon tetrabromide → 2-(Bromomethyl)-4-chloro-1-fluorobenzene

HRID 1066808Notes

Reaction equation

HRID 1066808 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[CH2:4]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:31]>C(OCC)C>[F:1][C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[CH2:4][Br:31]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 27736135-Chloro-2-fluorobenzyl alcohol

Product 1

HCID 27736262-(Bromomethyl)-4-chloro-1-fluorobenzeneYield 112.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 2-fluoro-5-chlorobenzyl alcohol (1.28 g, 7.97 mmol) in diethyl ether (26 ml) was treated with triphenylphosphine (2.72 g, 10.36 mmol), followed by carbon tetrabromide (3.44 g, 10.36 mmol). The resultant suspension was stirred for 3.5 hours, then filtered, washing with diethyl ether. The filtrate was concentrated, then passed through a plug of silica to remove triphenylphosphate. The residue was then purified by liquid chromatography affording 2.0 grams of a clear oil.

Workup

  1. filtrationfiltered
  2. washwashing with diethyl ether
  3. concentrationThe filtrate was concentrated
  4. customto remove triphenylphosphate
  5. customThe residue was then purified by liquid chromatography

Sources & evidence

ORD record
ord-276ce778c1a84462b18a055612b46bc5
Source dataset
uspto-grants-2001_06
Patent number
US06245761B1

Reaction notes

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