Carbon tetrabromide → 2-(Bromomethyl)-1-fluoro-4-nitrobenzene

HRID 1593063Notes

Reaction equation

HRID 1593063 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH2:4]O.[Br:13]C(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CCOCC>[Br:13][CH2:4][C:3]1[CH:6]=[C:7]([N+:10]([O-:12])=[O:11])[CH:8]=[CH:9][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 4437169(2-Fluoro-5-nitrophenyl)methanol

Product 1

HCID 103539672-(Bromomethyl)-1-fluoro-4-nitrobenzene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2-fluoro-5-nitrobenzyl alcohol (1 g, 5.84 mmol) in 25 mL ether, was added tetrabromomethane (3.87 g, 11.7 mmol), followed by triphenylphosphine (3.39 g, 11.7 mmol). The mixture was stirred at room temperature for 2 hours. The reaction was concentrated and the crude residue purified by column chromatography (silica, 10% EtOAc/hexane) to give pure 2-bromomethyl-1-fluoro-4-nitro-benzene.

Workup

  1. concentrationThe reaction was concentrated
  2. customthe crude residue purified by column chromatography (silica, 10% EtOAc/hexane)

Sources & evidence

ORD record
ord-123008a4e0ab40c187200a4446d788a1
Source dataset
uspto-grants-2007_11
Patent number
US07294635B2

Reaction notes

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