Triphenylphosphine → 4-Bromo-2-(bromomethyl)-1-chlorobenzene

HRID 500321Notes

Reaction equation

HRID 500321 reaction equation
[Br:1]N1C(=O)CCC1=O.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([CH2:17]O)[CH:11]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([CH2:17][Br:1])[CH:11]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 5074766(5-Bromo-2-chlorophenyl)methanol

Product 1

HCID 115582804-Bromo-2-(bromomethyl)-1-chlorobenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

4.0 g N-bromosuccinimide are slowly added to a solution of 5.0 g of 4-bromo-1-chloro-2-hydroxymethyl-benzene and 5.9 g triphenylphosphine in 50 mL of tetrahydrofuran chilled to 5° C. After 1 h stirring at ambient temperature the precipitate is filtered off, and the solvent is eliminated in vacuo. The residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 50:1).

Workup

  1. filtrationis filtered off
  2. customThe residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 50:1)

Sources & evidence

ORD record
ord-d40362f948634dbfaa7021ad47c5ebf7
Source dataset
uspto-grants-2010_08
Patent number
US07772191B2

Reaction notes

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