Hydrochloric Acid → HCID 11508827, compound

HRID 215664Notes

Reaction equation

HRID 215664 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.[N+:12]([C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1)([O-:14])=[O:13].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:19](=[O:20])[C:18]1[CH:17]=[CH:16][C:15]([N+:12]([O-:14])=[O:13])=[CH:23][CH:22]=1)(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 85024-Nitrobenzoyl chlorideHCID 959915'-Bromo-2'-hydroxyacetophenone2×

Product 1

HCID 11508827HCID 11508827, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5′-bromo-2′-hydroxyacetophenone (compound 1) (863 mg, 4.65 mmol) was added to a pyridine solution (20 ml) that contained 4-nitrobenzoyl chloride (1.00 g, 4.65 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-nitrobenzoic acid 2-acetyl-4-bromophenyl ester (compound 2). Yield: 1.57 g (yield constant: 92.7%) 1H NMR (300 MHz, CDCl3) δ 8.37 (s, 4H), 8.00 (s, 1H), 7.76-7.72 (m, 1H), 7.16 (d, J=8.7 Hz, 1H), 2.55 (s, 3H). MS m/z 365 (MH+).

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-225c1dd216054c80a40c00a970cdc7b6
Source dataset
uspto-grants-2012_06
Patent number
US08192717B2

Reaction notes

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