Bromine → 2-Bromo-1,3-diphenylbutan-1-one

HRID 25959Notes

Reaction equation

HRID 25959 reaction equation
[Br:1]Br.[CH3:3][CH:4]([CH2:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(OCC)C>[Br:1][CH:11]([CH:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH3:3])[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13]

Participants

4

Reactant 2

HCID 24408BromineHCID 1370653-Phenylbutyrophenone

Product 1

HCID 3448632-Bromo-1,3-diphenylbutan-1-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Bromine (0.02 mol) was added dropwise to a stirred solution of 2-(α-methylbenzyl)acetophenone (0.02 mol) in dry diethyl ether (20 ml) at 5° over one hour. The ether was removed in vacuo and the residue redissolved in ether (100 ml), washed with saturated sodium bicarbonate solution (2 × 100 ml) and then water (4 × 100 ml), and dried over anhydrous sodium sulphate. Removal of the solvent gave a solid which on recrystallisation from petroleum ether (40°-60°) gave 2-bromo-3-phenylbutyrophenone, m.p. 69°-71°.

Workup

  1. customThe ether was removed in vacuo
  2. dissolutionthe residue redissolved in ether (100 ml)
  3. washwashed with saturated sodium bicarbonate solution (2 × 100 ml)
  4. dry with materialwater (4 × 100 ml), and dried over anhydrous sodium sulphate
  5. customRemoval of the solvent
  6. customgave a solid which
  7. customon recrystallisation from petroleum ether (40°-60°)

Sources & evidence

ORD record
ord-748a261313fa44569f5d89675209ea8a
Source dataset
uspto-grants-1979_04
Patent number
US04147793

Reaction notes

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