Boron tribromide → Ethyl 3-(bromomethyl)phenoxyacetate

HRID 1741376Notes

Reaction equation

HRID 1741376 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([O:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)[Br:17]>ClCCl>[Br:17][CH2:2][C:3]1[CH:4]=[C:5]([O:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 18367402Ethyl [3-(hydroxymethyl)phenoxy]acetate

Product 1

HCID 11459982Ethyl 3-(bromomethyl)phenoxyacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-hydroxymethyl-1-ethoxycarbonylmethoxybenzene (1 g) in dichloromethane (10 ml) was added BBr3 (0.45 ml). After 1 hour, the solvent was evaporated in vacuo and the residue was dissolved in ethyl acetate. The organic layer was washed with NaHCO3 and brine. The dried solvent was evaporated in vacuo to give 3-bromomethyl-1-ethoxycarbonylmethoxybenzene (0.76 g). NMR (CDCl3, δ): 1.29 (3H, t, J=7 Hz), 4.24 (2H, d, J=7 Hz), 4.61 (2H, s), 5.00 (1H, d, J=3.0 Hz), 5.05 (1H, d, J=3.0 Hz), 6.7-7.1 (3H, m), 7.2-7.3 (1H, m)

Workup

  1. customthe solvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe organic layer was washed with NaHCO3 and brine
  4. customThe dried solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-93b1b64c9a5a44ce8317c9d9c79cee76
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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