Bromine → Methyl 2-(3-bromo-4-hydroxyphenyl)acetate

HRID 1752873Notes

Reaction equation

HRID 1752873 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[Br:13]Br>C(O)(=O)C>[Br:13][C:7]1[CH:6]=[C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:4]=[CH:3][C:2]=1[OH:1]

Participants

4

Reactant 2

HCID 24408BromineHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 10634081Methyl 2-(3-bromo-4-hydroxyphenyl)acetateYield 77.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Methyl 4-hydroxyphenylacetate (10.5 g, 63.0 mmol) was dissolved in acetic acid (200 mL) and the solution was stirred while bromine (150 mL, 0.463 M in acetic acid, 69.5 mmol) was added over 60 minutes. The mixture was stirred overnight and then concentrated by evaporation. Product was purified from the residue over 300 g of silica gel (hexanes/ethyl acetate 5:1) to give methyl 3-bromo-4-hydroxyphenylacetate (11.9 g).

Workup

  1. additionwas added over 60 minutes
  2. concentrationconcentrated by evaporation
  3. customProduct was purified from the residue over 300 g of silica gel (hexanes/ethyl acetate 5:1)

Sources & evidence

ORD record
ord-937ce24930bb41e197b0784c1fb96d06
Source dataset
uspto-grants-2015_10
Patent number
US09162986B2

Reaction notes

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