Hydrochloric Acid → Benzoic acid, 4-methoxy-, 2-acetyl-4-bromophenyl ester

HRID 215671Notes

Reaction equation

HRID 215671 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[CH3:12][O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1.Cl>N1C=CC=CC=1>[C:8]([C:6]1[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[O:11][C:18](=[O:19])[C:17]1[CH:21]=[CH:22][C:14]([O:13][CH3:12])=[CH:15][CH:16]=1)(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7477p-Anisoyl chlorideHCID 959915'-Bromo-2'-hydroxyacetophenone2×

Product 1

HCID 11674678Benzoic acid, 4-methoxy-, 2-acetyl-4-bromophenyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5′-bromo-2′-hydroxyacetophenone (compound 12) (1.80 g, 10.6 mmol) was added to a pyridine solution (40 ml) that contained 4-methoxybenzoyl chloride (2.01 g, 9.35 mmol) in an ice bath. The obtained mixture was reacted at room temperature for 30 minutes, and the reaction solution was then poured into 1 N hydrochloric acid under cooling on ice. The obtained mixture was intensively stirred. The obtained precipitate was collected by filtration, and the filtrate was then washed with purified water, so as to obtain a product of interest, 4-methoxybenzoic acid 2-acetyl-4-bromophenyl ester (compound 13). Yield: 3.15 g (yield constant: 96.5%) 1H NMR (300 MHz, CDCl3) δ 7.72 (d, J=7.5 Hz, 1H), 8.06 (d, J=7.2 Hz, 1H), 8.86 (s, 1H), 10.13 (s, 1H).

Workup

  1. customThe obtained mixture was reacted at room temperature for 30 minutes
  2. temperatureunder cooling on ice
  3. filtrationThe obtained precipitate was collected by filtration
  4. washthe filtrate was then washed with purified water

Sources & evidence

ORD record
ord-edcb51f8e09e40f495ada2de0721d14b
Source dataset
uspto-grants-2012_06
Patent number
US08192717B2

Reaction notes

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