1-Phenyl-1-propanone → 4-(1-(4-(2-Bromoethoxy)-3-fluorophenyl)-2-phenylbut-1-enyl)phenol

HRID 626136Notes

Reaction equation

HRID 626136 reaction equation
[Br:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=O)=[CH:7][C:6]=1[F:20].[C:21]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=O)[CH2:22][CH3:23]>>[Br:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[C:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:22][CH3:23])=[CH:7][C:6]=1[F:20]

Participants

3

Reactant 2

HCID 71481-Phenyl-1-propanoneHCID 89656059(4-(2-Bromoethoxy)-3-fluorophenyl)(4-hydroxyphenyl)methanone

Product 1

HCID 1212667244-(1-(4-(2-Bromoethoxy)-3-fluorophenyl)-2-phenylbut-1-enyl)phenolYield 99.6%

Procedure

Following general procedure of McMurry reaction as described in example 1, step B, (4-(2-bromoethoxy)-3-fluorophenyl)(4-hydroxyphenyl)methanone (311 mg, 0.917 mmol) was reacted with propiophenone (246 mg, 1.83 mmol) to give 403 mg desired product (99.6% yield, Z/E=1/1) as a beige solid.

Workup

  1. customgeneral procedure of McMurry reaction

Sources & evidence

ORD record
ord-bb1407722d11477b93b017d0f10e6362
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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