Benzhydrol → Benzhydryl 4-bromo-3-oxobutyrate

HRID 444557Notes

Reaction equation

HRID 444557 reaction equation
C=C1OC(=O)C1.BrBr.[CH:9]([OH:22])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Br:23][CH2:24][C:25](=[O:30])[CH2:26][C:27](Br)=[O:28]>C(Cl)Cl.C(N(CC)CC)C>[Br:23][CH2:24][C:25](=[O:30])[CH2:26][C:27]([O:22][CH:9]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:28]

Participants

7

Reactant 4

HCID 7037BenzhydrolHCID 12661DiketeneHCID 24408BromineHCID 128310484-Bromo-3-oxobutanoyl bromide

Product 1

HCID 15080911Benzhydryl 4-bromo-3-oxobutyrate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

In 10.5 ml of methylene chloride there were dissolved 2.1 g of diketene, and at a temperature not exceeding -30° C., a solution of 4.0 g of bromine in 12.5 ml of methylene chloride was added dropwise to the solution with stirring. After the dropwise addition was completed, the mixture was maintained at 0° C. for 10 minutes. Separately, 3.68 g of benzhydrol were dissolved in 25 ml of methylene chloride, followed by addition of 2.02 g of triethylamine. Under stirring at a temperature not exceeding -30° C., the solution of bromoacetoacetyl bromide prepared above was added dropwise. After the dropwise addition, the mixture was stirred at 0° C. for 40 minutes, at the end of which time it was washed with water. After drying over magnesium sulfate the solvent was distilled off under reduced pressure, whereupon 6.99 g of benzhydryl 4-bromo-3-oxobutyrate there were obtained.

Workup

  1. customexceeding -30° C.
  2. additionAfter the dropwise addition
  3. stirringUnder stirring at a temperature not
  4. customexceeding -30° C.
  5. additionabove was added dropwise
  6. additionAfter the dropwise addition
  7. stirringthe mixture was stirred at 0° C. for 40 minutes, at the end of which time it
  8. washwas washed with water
  9. dry with materialAfter drying over magnesium sulfate the solvent
  10. distillationwas distilled off under reduced pressure, whereupon 6.99 g of benzhydryl 4-bromo-3-oxobutyrate
  11. customthere were obtained

Sources & evidence

ORD record
ord-6588f45014f0496398f74ee17145e6d1
Source dataset
uspto-grants-1981_04
Patent number
US04264595

Reaction notes

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