Hydrogen Bromide → HCID 11063147, compound

HRID 1784675Notes

Reaction equation

HRID 1784675 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9]Br)=[CH:4][CH:3]=1.[OH2:12].Br.CS(C)=[O:16]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH:9]([OH:16])[OH:12])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 260Hydrogen BromideHCID 679Dimethyl SulfoxideHCID 962Water2×HCID 68303p-Chlorophenacyl bromide

Product 1

HCID 11063147HCID 11063147, compoundYield 70%

Procedure

A solution of 4′-chloro-2-bromoacetophenone (25.0 g, 107 mmol), water (1.92 mL, 107 mmol) and 47% hydrobromic acid (0.20 mL) in dimethylsulfoxide (160 mL) was stirred at 80° C. for 5 h. After the reaction mixture was poured into water, the precipitate was filtered, washed with diethylether and dried, affording 4′-chloro-2,2-dihydroxyacetophenone (14.0 g, 70%). 1H NMR (300 MHz, CDCl3), δ 5.92(1H, s), 7.45-7.52(2H, m), 8.05-8.20(2H, m).

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed with diethylether
  3. customdried

Sources & evidence

ORD record
ord-2588ad8fe3934c25819aac4bbb482aa5
Source dataset
uspto-grants-2009_03
Patent number
US07504411B2

Reaction notes

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