Diethyl Ether → 3-Bromo-1-(4-fluorophenyl)-1-phenylpropan-2-one

HRID 436938Notes

Reaction equation

HRID 436938 reaction equation
[Br:1]Br.[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11](=[O:13])[CH3:12])=[CH:6][CH:5]=1.CCOCC>C(O)(=O)C>[Br:1][CH2:12][C:11](=[O:13])[CH:10]([C:7]1[CH:6]=[CH:5][C:4]([F:3])=[CH:9][CH:8]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24408BromineHCID 125490341-(4-Fluorophenyl)-1-phenylpropan-2-one

Product 1

HCID 125490353-Bromo-1-(4-fluorophenyl)-1-phenylpropan-2-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Bromine (14.85 g) in acetic acid (200 ml.) was added dropwise to a solution of 1-p-fluorophenyl-1-phenyl-propan-2-one (20 lg.) in acetic acid (200 ml.) at 60° - 70°. After 30 minutes, the reaction mixture was poured on to ice. Isolation through ether in the usual manner gave crude 3-bromo-1-p-fluorophenyl-1-phenyl-propan-2-one (28 g) which was converted by the procedures described in Example 1 to 3-(N-Benzyl,N-methylamino)-1-p-fluorophenyl-1-phenyl-propan-2-ol (38%), m.p. 61° - 62°.

Workup

  1. additionthe reaction mixture was poured on to ice

Sources & evidence

ORD record
ord-bce068ffa4de4102b661f9a73d47d47a
Source dataset
uspto-grants-1977_06
Patent number
US04028415

Reaction notes

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