3,4-Bis(benzoyloxymethyl)benzyl bromide → 1-{5'-[3,4-Bis(benzoyloxymethyl)benzyloxy]-2,2'-diethylbiphenyl-4-yl}-1-propanone

HRID 584304Notes

Reaction equation

HRID 584304 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([C:9](=[O:12])[CH2:10][CH3:11])[CH:6]=[CH:5][C:4]=1[C:13]1[CH:18]=[C:17]([OH:19])[CH:16]=[CH:15][C:14]=1[CH2:20][CH3:21])[CH3:2].[C:22]([O:30][CH2:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][C:39]=1[CH2:40][O:41][C:42](=[O:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[CH2:35]Br)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[C:22]([O:30][CH2:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][C:39]=1[CH2:40][O:41][C:42](=[O:49])[C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)[CH2:35][O:19][C:17]1[CH:16]=[CH:15][C:14]([CH2:20][CH3:21])=[C:13]([C:4]2[CH:5]=[CH:6][C:7]([C:9](=[O:12])[CH2:10][CH3:11])=[CH:8][C:3]=2[CH2:1][CH3:2])[CH:18]=1)(=[O:29])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 223456183,4-Bis(benzoyloxymethyl)benzyl bromideHCID 223456221-(2,2'-Diethyl-5'-hydroxybiphenyl-4-yl)-1-propanone

Product 1

HCID 223456371-{5'-[3,4-Bis(benzoyloxymethyl)benzyloxy]-2,2'-diethylbiphenyl-4-yl}-1-propanone

Procedure

In a manner similar to that of Example 1(o), by reacting 1.67 g (5.9 mmol) of 1-(2,2′-diethyl-5′-hydroxybiphenyl-4-yl)-1-propanone with 2.73 g (6.2 mmol) of 3,4-bis(benzoyloxymethyl)benzyl bromide, and after purification by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (95/5), 1.88 g (50%) of the expected product are obtained in the form of an oil.

Workup

  1. customafter purification by chromatography on a column of silica
  2. washeluted with a mixture of heptane and ethyl acetate (95/5), 1.88 g (50%) of the expected product
  3. customare obtained in the form of an oil

Sources & evidence

ORD record
ord-76a36125535c45ae9e110bcc212e190f
Source dataset
uspto-grants-2005_08
Patent number
US06924400B2

Reaction notes

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