1-(3-Fluoro-4-hydroxyphenyl)propan-1-one → 4-(1-(4-(2-Chloroethoxy)phenyl)-1-(4-hydroxyphenyl)but-1-en-2-yl)-2-fluorophenol

HRID 626140Notes

Reaction equation

HRID 626140 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9](=O)[CH2:10][CH3:11])[CH:5]=[CH:6][C:7]=1[OH:8].[Cl:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)=O)=[CH:19][CH:18]=1>>[Cl:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)=[C:9]([C:4]2[CH:5]=[CH:6][C:7]([OH:8])=[C:2]([F:1])[CH:3]=2)[CH2:10][CH3:11])=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 133224411-(3-Fluoro-4-hydroxyphenyl)propan-1-oneHCID 89656364[4-(2-Chloroethoxy)phenyl](4-hydroxyphenyl)methanone

Product 1

HCID 1235113284-(1-(4-(2-Chloroethoxy)phenyl)-1-(4-hydroxyphenyl)but-1-en-2-yl)-2-fluorophenolYield 88%

Procedure

Following general procedure of McMurry reaction as described in example 1, step B, 1-(3-fluoro-4-hydroxyphenyl)propan-1-one (255 mg, 1.52 mmol) was reacted with (4-(2-chloroethoxy)phenyl)(4-hydroxyphenyl)methanone (629 mg, 2.27 mmol) to give 549 mg desired product (88% yield).

Workup

  1. customgeneral procedure of McMurry reaction

Sources & evidence

ORD record
ord-749c09980bb74d24a11d73a746bdcdcd
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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