Triphenylphosphine → 3-Chloro-5-iodobenzyl bromide

HRID 2101516Notes

Reaction equation

HRID 2101516 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.[Cl:22][C:23]1[CH:24]=[C:25]([CH2:30]O)[CH:26]=[C:27]([I:29])[CH:28]=1>C(Cl)Cl>[Br:20][CH2:30][C:25]1[CH:26]=[C:27]([I:29])[CH:28]=[C:23]([Cl:22])[CH:24]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 24408BromineHCID 68865549(3-Chloro-5-iodophenyl)methanol

Product 1

HCID 578015153-Chloro-5-iodobenzyl bromideYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred ice-cooled solution of triphenylphosphine in 10 mL of CH2Cl2 was added dropwise a solution of bromine in 5 ml of CH2Cl2. After the reaction mixture was stirred at room temperature for 30 min and cooled at ice bath temperature, a solution of the above (3-chloro-5-iodo-phenyl)-methanol in 15 ml of CH2Cl2 was added dropwise. The reaction mixture was stirred 0° C. for another 1 h and concentrated. The residue was washed with hexane several times and the combined hexane layer was concentrated to give 1-bromomethyl-3-chloro-5-iodo-benzene (1.2 g, 97%).

Workup

  1. temperaturecooled at ice bath temperature
  2. stirringThe reaction mixture was stirred 0° C. for another 1 h
  3. concentrationconcentrated
  4. washThe residue was washed with hexane several times
  5. concentrationthe combined hexane layer was concentrated

Sources & evidence

ORD record
ord-2c3e5eb2452240d98dd0c2f31121fe28
Source dataset
uspto-grants-2009_08
Patent number
US07572921B2

Reaction notes

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