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

HRID 1752882Notes

Reaction equation

HRID 1752882 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].[CH3:13]O>S(Cl)(Cl)=O>[CH3:13][O:11][C:10](=[O:12])[CH2:9][C:4]1[CH:5]=[CH:6][C:7]([OH:8])=[C:2]([Br:1])[CH:3]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 27696283-Bromo-4-hydroxyphenylacetic acid

Product 1

HCID 10634081Methyl 2-(3-bromo-4-hydroxyphenyl)acetate

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideCatalyst

Procedure

3-Bromo-4-hydroxyphenylacetic acid (12.0 g, 0.052 mol) was dissolved in methanol and the solution was stirred at room temperature while thionyl chloride (ten drops) was added. The mixture was stirred for two hours and then concentrated under reduced pressure. The residue was taken up in saturated aqueous sodium bicarbonate and the solution extracted with diethyl ether (×3). The organic layers were collected, washed with water and brine, dried over MgSO4 and concentrated in vacuo to give methyl-3-bromo-4-hydroxyphenylacetate as a golden oil (12.6 g).

Workup

  1. additionwas added
  2. concentrationconcentrated under reduced pressure
  3. extractionthe solution extracted with diethyl ether (×3)
  4. customThe organic layers were collected
  5. washwashed with water and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bffefbcbb7ed44f995966c9f4e0a5b85
Source dataset
uspto-grants-2015_10
Patent number
US09162986B2

Reaction notes

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