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

HRID 1264614Notes

Reaction equation

HRID 1264614 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH2:8]O)[CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:33]>C(Cl)Cl>[Br:33][CH2:8][C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[N+:10]([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 12016493(5-Fluoro-2-nitrophenyl)methanol

Product 1

HCID 105616432-(Bromomethyl)-4-fluoro-1-nitrobenzeneYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-Fluoro-2-nitrophenyl) methanol (0.3 g, 1.75 mmol) in methylene chloride (5 mL0 was added triphenylphosphine (0.52 g, 2.01 mmol) and carbon tetrabromide (0.66 g, 2.01 mmol). After 3 hours, the reaction was concentrated and chromatographed using 3:1 hexane:ethyl acetate as eluant to provide 0.38 g (93%) of the desired product as white crystals. mp 38-41° C. Anal Calc'd for C7H5N3O2FBr: C, 35.93; H, 2.15; N, 5.99. Found: C, 35.97; H, 2.12; N, 5.91.

Workup

  1. concentrationthe reaction was concentrated
  2. customchromatographed

Sources & evidence

ORD record
ord-43fddb9e209b4648ad9915a95777cabd
Source dataset
uspto-grants-2003_04
Patent number
US06544984B1

Reaction notes

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