Methanol → Methyl 3-bromo-5-hydroxybenzoate

HRID 1686436Notes

Reaction equation

HRID 1686436 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:9]C(O)=O)[CH:5]=[C:6]([OH:8])[CH:7]=1.[C:13](Cl)(=[O:15])C.C[OH:18]>>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([OH:8])[CH:7]=1)[C:9]([O:15][CH3:13])=[O:18]

Participants

4

Reactant 3

HCID 887MethanolHCID 6367Acetyl chlorideHCID 667341662-(3-Bromo-5-hydroxyphenyl)acetic acid

Product 1

HCID 53216607Methyl 3-bromo-5-hydroxybenzoate

Procedure

The product from example 55 step (v) (3.24 g) was added to a preformed solution of methanol (200 ml) and acetyl chloride (20 ml) and stirred at RT overnight. The mixture was evaporated under reduced pressure to give an oil. The oil was purified by flash column chromatography (eluent 1:1 ether/isohexane) to give the subtitle compound (3.16 g).

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. customto give an oil
  3. customThe oil was purified by flash column chromatography (eluent 1:1 ether/isohexane)

Sources & evidence

ORD record
ord-a0860aa83c5c4042aecf3d2a0a64eb5e
Source dataset
uspto-grants-2012_04
Patent number
US08148572B2

Reaction notes

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