Hydrochloric Acid → 1-(5-Bromo-2-hydroxyphenyl)propan-1-one

HRID 2096541Notes

Reaction equation

HRID 2096541 reaction equation
C([O:5][C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][CH:7]=1)(=O)CC.[Cl-].[Al+3].[Cl-].[Cl-].Cl>>[Br:12][C:9]1[CH:10]=[CH:11][C:6]([OH:5])=[C:7]([C:6](=[O:5])[CH2:7][CH3:8])[CH:8]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 90205p-Bromophenyl propionateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 7364091-(5-Bromo-2-hydroxyphenyl)propan-1-one

Procedure

4-Bromophenyl propionate (34 g, 0.15 mmol) and aluminum chloride (44 g, 0.3 mmol) were heated together at 100° C. for 30 mins. The solution became dark and hydrogen chloride gas was evolved. After cooling, the reaction mixture was carefully poured into ice water, and the resulting mixture was extracted with dichloromethane. The organic layer was washed with brine, dried and concentrated to give the residue, which was purified by column chromatography to give 1-(5-bromo-2-hydroxyphenyl)propan-1-one. (20 g, 59%) 1H NMR (CDCl3, 400 MHz): 1.24 (t, 3H), 2.98-3.04 (m, 2H), 6.88 (d, 1H), 7.52 (t, 1H), 7.76 (s, 1H).

Workup

  1. temperatureAfter cooling
  2. extractionthe resulting mixture was extracted with dichloromethane
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto give the residue, which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-182f1a47ed80402d9cbacf46fb3fbd0f
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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