Hydrochloric Acid → Methyl 4-(acetyloxy)-3-bromobenzoate

HRID 41172Notes

Reaction equation

HRID 41172 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].N1C=CC=CC=1.[C:19](Cl)(=[O:21])[CH3:20].Cl>C(Cl)Cl.O>[C:19]([O:12][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[Br:1])(=[O:21])[CH3:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6367Acetyl chlorideHCID 4778958Methyl 3-bromo-4-hydroxybenzoate

Product 1

HCID 45037033Methyl 4-(acetyloxy)-3-bromobenzoateYield 94.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of methyl 3-bromo-4-hydroxybenzoate (270 g, 1168 mmol) in DCM (1.5 L) was added pyridine (150 mL). Acetyl chloride (87 mL, 1227 mmol) was then added dropwise at room temperature and under nitrogen. The mixture was left to stir for 2 h at room temperature. Water (1 L) was then added followed by HCl 2N until pH 1. The organic layer was then washed with water, brine, dried over MgSO4, filtered and evaporated to dryness to afford methyl 4-acetoxy-3-bromobenzoate (300 g, 94%) as a white powder.

Workup

  1. waitThe mixture was left
  2. washThe organic layer was then washed with water, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-b1db9f58bdde4b459567629dac1f7cd7
Source dataset
uspto-grants-2013_09
Patent number
US08530470B2

Reaction notes

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