Phosphorus tribromide → 1-Bromo-3-(bromomethyl)-5-fluorobenzene

HRID 1634994Notes

Reaction equation

HRID 1634994 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH2:5]O.P(Br)(Br)[Br:12]>C(Cl)Cl.CCOCC>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH2:5][Br:12]

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 2769402(3-Bromo-5-fluorophenyl)methanol

Product 1

HCID 235096191-Bromo-3-(bromomethyl)-5-fluorobenzene

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-Bromo-5-fluorobenzyl alcohol (2.3 g, 0.011 mole) in CH2Cl2 (15 mL) was added 12.4 mL of 1.0M PBr3 (3.33 g, 0.0123 mole) in CH2Cl2, stirred for 3 hr, diluted with ether (100 mL), washed with H2O (50 ml, 3×), dried over MgSO4, concentrated, and purified by column chromatography using 1:9 ethyl acetate/hexane as an eluant solvent system. 3-Bromo-5-fluorobenzyl bromide was obtained as a white crystalline material was obtained, mp 41-43° C. 1H NMR (DMSO-d6) δ4.69 (s, 2H), 7.52(d, 1H, J=1.76 Hz) 7.54(d, 1H, J=1.91 Hz), 7.56(s, 1H); MS(EI): M+. m/z 266; Anal. Calc. For C7H5Br2F: C, 31.38, H, 1.88. Found: C, 31.75, H, 1.78.

Workup

  1. washwashed with H2O (50 ml, 3×)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-72714f5caffe432ea2fdbab132af2017
Source dataset
uspto-grants-2003_01
Patent number
US06509334B1

Reaction notes

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