Bromomethyl 4-methoxyphenyl ketone → 2-(5-Benzyloxy-2-vinylphenoxy)-1-(4-methoxyphenyl)ethanone

HRID 254911Notes

Reaction equation

HRID 254911 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[CH2:16])=[C:11]([O:17][CH2:18][C:19]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)=C)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O:36]C1C=CC(C=O)=C(O)C=1)C1C=CC=CC=1.CC([O-])(C)C.[K+].BrCC(C1C=CC(OC)=CC=1)=O>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[CH2:16])=[C:11]([CH:10]=1)[O:17][CH2:18][C:19]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)=[O:36])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 5612354-Benzyloxy-2-hydroxybenzaldehydeHCID 23665647Potassium tert-butoxideHCID 595921064-Benzyloxy-2-[2-(4-methoxyphenyl)allyloxy]-1-vinylbenzene

Product 1

HCID 498213242-(5-Benzyloxy-2-vinylphenoxy)-1-(4-methoxyphenyl)ethanoneYield 74%

Procedure

Alternatively, the compound 2 can be obtained by reacting 4-benzyloxy-2-hydroxybenzaldehyde with a mixture of MTPPB and t-BuOK, followed by reaction with 2-bromo-4′-methoxyacetophenone, and the resultant mixture, instead of being subjected to purification to afford compound 2a, was continuously reacted with a mixture of MTPPB and t-BuOK in THF, giving a one pot yield of 74%.

Workup

  1. customthe resultant mixture, instead of being subjected to purification

Sources & evidence

ORD record
ord-04e42c318f6241ceb779ed124bd91f80
Source dataset
uspto-grants-2011_01
Patent number
US07875736B2

Reaction notes

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