4-Hydroxybenzaldehyde → HCID 68745335, compound

HRID 2378566Notes

Reaction equation

HRID 2378566 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:16][CH2:17][C:18]([O:20]C)=[O:19])[CH:5]=[CH:6][C:7]=1[O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].BrC1C=C(C=CC(O)=O)C=CC=1O.OC1C=CC(C=O)=CC=1.N1C=CN=C1.[Si:49](Cl)([C:52]([CH3:55])([CH3:54])[CH3:53])([CH3:51])[CH3:50]>>[Br:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]([O:20][Si:49]([C:52]([CH3:55])([CH3:54])[CH3:53])([CH3:51])[CH3:50])=[O:19])[CH:5]=[CH:6][C:7]=1[O:8][Si:9]([C:12]([CH3:14])([CH3:13])[CH3:15])([CH3:10])[CH3:11]

Participants

6

Reactant 5

HCID 1264-HydroxybenzaldehydeHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 209865373-(3-Bromo-4-hydroxyphenyl)prop-2-enoic acidHCID 22559225HCID 22559225, compound

Product 1

HCID 68745335HCID 68745335, compound

Procedure

According to the procedure described in the synthesis method of Intermediate 43, 3-[3-bromo-4-hydroxylphenyl]acrylic acid (12.01 g) obtainable from 4-hydroxybenzaldehyde (TCI) by a method known from literature (Y. Nagao et al., Tetrahedron Lett., 1980, p. 4931) was reacted with imidazole (16.01 g) and t-butyldimethylsilyl chloride (7.43 g) and treated to obtain the title compound (Intermediate Ac-1, 17.43 g).

Workup

  1. additiontreated

Sources & evidence

ORD record
ord-2de06a2b2dc7440da1c3ee0ccfe2f0e7
Source dataset
uspto-grants-2008_12
Patent number
US07470807B2

Reaction notes

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