Bromine → 3-BROMO-4-(4-FLUOROPHENYL)-4-OXOBUTANOIC ACID

HRID 903432Notes

Reaction equation

HRID 903432 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:7])=[CH:4][CH:3]=1.[Br:15]Br>C(O)(=O)C>[Br:15][CH:8]([C:6](=[O:7])[C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:14][CH:13]=1)[CH2:9][C:10]([OH:12])=[O:11]

Participants

4

Reactant 2

HCID 24408BromineHCID 1013593-(4-Fluorobenzoyl)propionic acid

Product 1

HCID 38961393-BROMO-4-(4-FLUOROPHENYL)-4-OXOBUTANOIC ACID

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 19.62 g. of 3-(p-fluorobenzoyl)propionic acid in 100 ml. of acetic acid, is added 16 g. of bromine. The mixture is stirred for 18 hours and then the solvent is removed. Ice and water are added to the residue and the mixture is filtered. The solid is washed with water and then dissolved in 80 ml. of acetone. The solution is diluted with 400 ml. of hexane and allowed to evaporate, at room temperature, to a volume of 125 ml. A 100 ml. portion of hexane is added and the mixture is filtered, giving 24.6 g. of the desired product as tan crystals, m.p. 131°-135° C.

Workup

  1. customthe solvent is removed
  2. additionIce and water are added to the residue
  3. filtrationthe mixture is filtered
  4. washThe solid is washed with water
  5. dissolutiondissolved in 80 ml
  6. additionThe solution is diluted with 400 ml
  7. customto evaporate, at room temperature, to a volume of 125 ml
  8. additionportion of hexane is added
  9. filtrationthe mixture is filtered
  10. customgiving 24.6 g

Sources & evidence

ORD record
ord-027d8f2861574c6a9afa6eb8802a6d03
Source dataset
uspto-grants-1980_10
Patent number
US04226775

Reaction notes

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