Phosphorus tribromide → Methyl 2-(2-(2-Propyl)-4-Bromomethyl-Phenoxy)-2-(3-Chlorophenyl)Acetate

HRID 37244Notes

Reaction equation

HRID 37244 reaction equation
[CH3:1][CH:2]([C:4]1[CH:22]=[C:21]([CH2:23]O)[CH:20]=[CH:19][C:5]=1[O:6][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=1)[C:8]([O:10][CH3:11])=[O:9])[CH3:3].P(Br)(Br)[Br:26]>C(Cl)(Cl)(Cl)Cl>[CH3:1][CH:2]([C:4]1[CH:22]=[C:21]([CH2:23][Br:26])[CH:20]=[CH:19][C:5]=1[O:6][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=1)[C:8]([O:10][CH3:11])=[O:9])[CH3:3]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 54146549Methyl 2-(2-(2-Propyl)-4-Hydroxymethyl-Phenoxy)-2-(3-Chlorophenyl)Acetate

Product 1

HCID 54090485Methyl 2-(2-(2-Propyl)-4-Bromomethyl-Phenoxy)-2-(3-Chlorophenyl)AcetateYield 81.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 0.110 g (0.31 mmol) of the product of Step A dissolved in 1.0 mL of carbon tetrachloride was added 0.03 mL (1.6 mmol) of phosphorous tribromide and the reaction mixture was stirred at room temperature for 10 minutes. Carbon tetrachloride was evaporated from the reaction mixture several times to remove the hydrogen bromide, then the residue was purified on a silica gel flash chromatography column eluted with 15% EtOAc-hexane. The purified fractions were evaporated in vacuo affording 0.104 g (80%) of the title compound.

Workup

  1. customCarbon tetrachloride was evaporated from the reaction mixture several times
  2. customto remove the hydrogen bromide
  3. customthe residue was purified on a silica gel flash chromatography column
  4. washeluted with 15% EtOAc-hexane
  5. customThe purified fractions were evaporated in vacuo

Sources & evidence

ORD record
ord-9a742bf544ec495cb4f7cd7d15b39a66
Source dataset
uspto-grants-1995_05
Patent number
US05420133

Reaction notes

Loading…