Carbon tetrabromide → 2-(Bromomethyl)-4-chloro-1-fluorobenzene
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
Product 1
Reagents, catalysts & solvents 1
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
- filtrationfiltered
- washwashing with diethyl ether
- concentrationThe filtrate was concentrated
- customto remove triphenylphosphate
- 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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