Methanol → Methyl 4-Bromo-3-hydroxybenzoate

HRID 967441Notes

Reaction equation

HRID 967441 reaction equation
S(Cl)(Cl)=O.[Br:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][C:7]=1[OH:15].[CH3:16]O>>[CH3:16][O:11][C:10](=[O:12])[C:9]1[CH:13]=[CH:14][C:6]([Br:5])=[C:7]([OH:15])[CH:8]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 64209734-Bromo-3-hydroxybenzoic acid

Product 1

HCID 6425184Methyl 4-Bromo-3-hydroxybenzoate

Conditions

Temperature
50 °C

Procedure

1.5 ml of thionyl chloride was added to 40 ml of MeOH at 0° C. The solution was stirred for 10 min and 5 g of 4-Bromo-3-hydroxy-benzoic acid was added. The reaction was stirred for 16 h at RT then heated to 50° C. for 3 h. The solvents were removed under reduced pressure. The residue was used directly in the next step. Yield 5.92 g

Workup

  1. stirringThe reaction was stirred for 16 h at RT
  2. customThe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-0733f3ba7ae14160b572947e21105d09
Source dataset
uspto-grants-2005_10
Patent number
US06953857B2

Reaction notes

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