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

HRID 930856Notes

Reaction equation

HRID 930856 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[Br:14]Br>C(O)(=O)C>[Br:14][C:7]1[CH:6]=[C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:4]=[CH:3][C:2]=1[OH:1]

Participants

4

Reactant 2

HCID 24408BromineHCID 28310Ethyl 4-hydroxyphenylacetate

Product 1

HCID 18620106Ethyl 2-(3-bromo-4-hydroxyphenyl)acetateYield 94.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of ethyl 2-(4-hydroxyphenyl)acetate (Alfa, 2.70 g, 15 mmol) in acetic acid (20 mL) was added drop wise over 15 minutes a solution of bromine (0.773 mL, 15.00 mmol) in acetic acid (15 mL). The mixture was stirred at ambient temperature for 30 minutes and evaporated. Purification by chromatography (silica gel, 10-20% ethyl acetate in hexane) afforded the title compound (3.66 g, 94%).

Workup

  1. customevaporated
  2. customPurification by chromatography (silica gel, 10-20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-22f2340ee5a44789b9c3ae88d3ba4f47
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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