1-Phenyl-1-propanone → 4-(1-(4-(2-Chloroethoxy)phenyl)-2-phenylbut-1-enyl)-2-fluorophenol

HRID 626146Notes

Reaction equation

HRID 626146 reaction equation
[Cl: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])=[C:15]([F:20])[CH:14]=2)=O)=[CH:7][CH:6]=1.[C:21]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=O)[CH2:22][CH3:23]>>[Cl: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])=[C:15]([F:20])[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][CH:6]=1

Participants

3

Reactant 2

HCID 71481-Phenyl-1-propanoneHCID 89656051(4-(2-Chloroethoxy)phenyl)(3-fluoro-4-hydroxyphenyl)methanone

Product 1

HCID 1232404234-(1-(4-(2-Chloroethoxy)phenyl)-2-phenylbut-1-enyl)-2-fluorophenol

Procedure

Following general procedure of McMurry reaction as described in example 1, step B, (4-(2-chloroethoxy)phenyl)(3-fluoro-4-hydroxyphenyl)methanone (350 mg, 1.19 mmol) was reacted with propiophenone (319 mg, 2.38 mmol) to give the desired product (quant.) as a yellow solid.

Workup

  1. customgeneral procedure of McMurry reaction

Sources & evidence

ORD record
ord-b03ec1d027cc4f6cab9ca746f37f3d73
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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