Hydrochloric Acid → 2-Bromo-4'-(4-fluoro-phenyl)-acetophenone

HRID 2397365Notes

Reaction equation

HRID 2397365 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.[Br:18][CH2:19][C:20](Br)=[O:21].Cl>C(Cl)CCl>[Br:18][CH2:19][C:20]([C:15]1[CH:16]=[CH:17][C:12]([C:9]2[CH:8]=[CH:7][C:6]([F:5])=[CH:11][CH:10]=2)=[CH:13][CH:14]=1)=[O:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 94614-FluorobiphenylHCID 61147Bromoacetyl bromideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 135319772-Bromo-4'-(4-fluoro-phenyl)-acetophenoneYield 60.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

44 gm (0.33 mol) of aluminum chloride were added in small portions to a solution of 51.7 gm (0.3 mol) of 4-fluoro-biphenyl and 66.6 gm (0.33 mol) of bromoacetyl bromide in 150 cc of ethylene chloride, while cooling the solution on an ice-salt bath, and the mixture was then stirred at room temperature for two hours. Thereafter, the reaction mixture was admixed with ice and hydrochloric acid, and the organic phase was separated, washed with water, dried with sodium sulfate and evaporated. The residue was recrystallized from 250 cc of carbon tetrachloride, yielding 53 gm (60% of theory) of 2-bromo-4'-(4-fluoro-phenyl)-acetophenone, m.p. 102°-103° C.

Workup

  1. temperaturewhile cooling the solution on an ice-salt bath
  2. customthe organic phase was separated
  3. washwashed with water
  4. dry with materialdried with sodium sulfate
  5. customevaporated
  6. customThe residue was recrystallized from 250 cc of carbon tetrachloride

Sources & evidence

ORD record
ord-79525ae26a7d4f14911246b51cf2ca72
Source dataset
uspto-grants-1977_05
Patent number
US04021479

Reaction notes

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