Methanol → Methyl 3-(2-bromoacetyl)-4-hydroxybenzoate

HRID 351141Notes

Reaction equation

HRID 351141 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[OH:14])[C:8]([OH:10])=[O:9])=[O:4].S(Cl)(Cl)=O.[CH3:19]O>>[Br:1][CH2:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[OH:14])[C:8]([O:10][CH3:19])=[O:9])=[O:4]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 135735143-(Bromoacetyl)-4-hydroxybenzoic acid

Product 1

HCID 18175087Methyl 3-(2-bromoacetyl)-4-hydroxybenzoate

Procedure

The compound obtained in Step B (27.4 mmol) is dissolved in 150 ml of MeOH, and 54.8 mmol of thionyl chloride are added dropwise in the cold state. The mixture is then stirred for 1 hour at ambient temperature and then for 2 hours at reflux. After evaporating off the methanol and the thionyl chloride, the oily residue is taken up in AcOEt, washed with water and then dried over MgSO4. The solvent is evaporated off under reduced pressure and the solid obtained is recrystallised.

Workup

  1. temperaturefor 2 hours at reflux
  2. customAfter evaporating off the methanol
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. customThe solvent is evaporated off under reduced pressure
  6. customthe solid obtained
  7. customis recrystallised

Sources & evidence

ORD record
ord-6246a818af604b52a2092ec5b5d538cf
Source dataset
uspto-grants-2007_02
Patent number
US07183318B2

Reaction notes

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