Hydrochloric Acid → Methyl 3-acetyl-5-bromo-4-hydroxybenzoate

HRID 41177Notes

Reaction equation

HRID 41177 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[OH:14])[C:7]([O:9][CH3:10])=[O:8])(=[O:3])[CH3:2].N1C=CC=CC=1.[Br:21]Br.Cl>C(Cl)Cl>[C:1]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([Br:21])[C:13]=1[OH:14])[C:7]([O:9][CH3:10])=[O:8])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 24408BromineHCID 12332833Methyl 3-acetyl-4-hydroxybenzoate

Product 1

HCID 15818980Methyl 3-acetyl-5-bromo-4-hydroxybenzoateYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of methyl 3-acetyl-4-hydroxybenzoate (240 g, 1236 mmol) in DCM (2 L) was added pyridine (0.400 L, 4944 mmol) followed by a dropwise addition of dibromine (0.070 L, 1360 mmol) at 0° C. The reaction mixture was stirred at room temperature for 2 h then cooled to 5° C. and HCl 4N (0.927 L, 3708 mmol) was added dropwise. The organic phase was separated, dried over MgSO4, filtered and concentrated to afford a brown solid which was stirred in ether/petroleum ether (1:1, 1 L) for 1 hr. The solid was collected by filtration and dried to afford methyl 3-acetyl-5-bromo-4-hydroxybenzoate (270 g, 80%) as a beige powder. Mass Spectrum: m/z [M+H]+=273.

Workup

  1. temperaturethen cooled to 5° C.
  2. customThe organic phase was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford a brown solid which
  7. filtrationThe solid was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-0a224cdee7864ed0846496f8cfeb7f5e
Source dataset
uspto-grants-2013_09
Patent number
US08530470B2

Reaction notes

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