Water → 1-(3-Bromo-4-hydroxyphenyl)ethanone

HRID 68596Notes

Reaction equation

HRID 68596 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)=[O:3].[Br:11]Br.O>C(O)(=O)C>[Br:11][C:6]1[CH:5]=[C:4]([C:2](=[O:3])[CH3:1])[CH:9]=[CH:8][C:7]=1[OH:10]

Participants

5

Reactant 3

HCID 962WaterHCID 74694'-HydroxyacetophenoneHCID 24408Bromine

Product 1

HCID 6080941-(3-Bromo-4-hydroxyphenyl)ethanoneYield 39.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 4-hydroxyacetophenone (6.8 g, 0.05 mol, 1 eq) in 60% acetic acid (50 mL), was added a solution of bromine (2.6 mL, 0.05 mol, 1 eq) in 80% acetic acid (20 mL). After stirring at room temperature for 30 min, the reaction mixture was poured into 100 mL of cold water. The solid was filtered and the filtrate was further diluted with 500 mL of cold water. The white precipitate was collected by filtration, washed with water and dried under vacuum to afford 4.2 g (39%) of 1-(3-bromo-4-hydroxyphenyl)ethanone (15) as white solid. 1HNMR (CDCl3, 400 MHz): δ 8.15 (s, 1H), 7.86 (d, 1H), 7.18 (d, 1H), 5.96 (s, 1H), 2.56 (s, 3H). MS (ES-API): M+1=216.9. HPLC (Method B) tR=2.48 min.

Workup

  1. filtrationThe solid was filtered
  2. additionthe filtrate was further diluted with 500 mL of cold water
  3. filtrationThe white precipitate was collected by filtration
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-6eddd28ac4fb4e4c8c503c75995f29ea
Source dataset
uspto-grants-2014_09
Patent number
US08822467B2

Reaction notes

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