Carbon tetrabromide → Methanesulfonic acid 2-bromomethyl-5-methylphenyl ester

HRID 889248Notes

Reaction equation

HRID 889248 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[O:10][S:11]([CH3:14])(=[O:13])=[O:12].C(Br)(Br)(Br)[Br:16].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[Br:16][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[O:10][S:11]([CH3:14])(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 86638980Methanesulfonic acid 2-hydroxymethyl-5-methylphenyl ester

Product 1

HCID 86638983Methanesulfonic acid 2-bromomethyl-5-methylphenyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methanesulfonic acid 2-hydroxymethyl-5-methylphenyl ester (864 mg, 4 mmol) in DCM (45 mL) is added CBr4 (2.0 g, 6 mmol) and PPh3 (1.57 g, 6 mmol). The mixture is stirred at RT for 6 h. The solvent is removed and the residue is purified to give the title compound as a solid.

Workup

  1. customThe solvent is removed
  2. customthe residue is purified

Sources & evidence

ORD record
ord-65b1e38750a7478f928d025ca4b99136
Source dataset
uspto-grants-2012_08
Patent number
US08252820B2

Reaction notes

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