Citric Acid → 1-(2-Bromo-4-fluorophenyl)-2-phenylethanone

HRID 1834856Notes

Reaction equation

HRID 1834856 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[C:4]#N.[CH2:11]([Mg]Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Mg].C(Cl)C1C=CC=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)[OH:32]>CCOCC>[Br:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[C:4](=[O:32])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 5

HCID 311Citric AcidHCID 7503Benzyl ChlorideHCID 1189392-Bromo-4-fluorobenzonitrileHCID 5462224MagnesiumHCID 178418336HCID 178418336, compound

Product 1

HCID 205595051-(2-Bromo-4-fluorophenyl)-2-phenylethanone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2-bromo-4-fluorobenzonitrile, 6.0 g. (0.03 mole) in 35 ml. of absolute ether is added dropwise to a stirred solution of benzylmagnesium chloride prepared from 2.9 g. (0.12 g. atom) of magnesium turnings and 15.2 g. (0.12 mole) of benzyl chloride in 65 ml. of absolute ether in a nitrogen atmosphere. The mixture is stirred at room temperature for about 18 hours. After cooling in an ice-bath, the adduct is hydrolyzed by the dropwise addition of 100 ml. of 0.5 M. citric acid. The organic phase is separated and the aqueous phase re-extracted with several portions of benzene. The combined organic layers are extracted with 45 ml. of ice-cold 6 N hydrochloric acid in several portions and the combined acid extracts are heated on the steam bath for 45 minutes. The product separates as an oil and is extracted into benzene. Evaporation of the washed and dried benzene extract leaves the yellow oily product that is purified by distillation; b.p. 112°-115° C./0.05 mm.

Workup

  1. customprepared from 2.9 g
  2. temperatureAfter cooling in an ice-bath
  3. additionthe adduct is hydrolyzed by the dropwise addition of 100 ml
  4. customThe organic phase is separated
  5. extractionthe aqueous phase re-extracted with several portions of benzene
  6. extractionThe combined organic layers are extracted with 45 ml
  7. temperatureof ice-cold 6 N hydrochloric acid in several portions and the combined acid extracts are heated on the steam bath for 45 minutes
  8. extractionis extracted into benzene
  9. customEvaporation of the
  10. washwashed
  11. extractiondried benzene extract
  12. customleaves the yellow oily product that
  13. distillationis purified by distillation

Sources & evidence

ORD record
ord-b3dd972a733a4e7ebeafc446e66ef64f
Source dataset
uspto-grants-1978_01
Patent number
US04071570

Reaction notes

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