4-Benzyloxy-phenylboronic acid → 6-(4-Benzyloxy-phenyl)-4-hydroxy-2-oxo-2H-chromene-3-carboxylic acid methyl ester

HRID 2190908Notes

Reaction equation

HRID 2190908 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6](=[O:17])[O:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][C:11](Br)=[CH:10][CH:9]=2)=[O:4].[CH2:18]([O:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[CH3:1][O:2][C:3]([C:5]1[C:6](=[O:17])[O:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][C:11]([C:29]1[CH:30]=[CH:31][C:26]([O:25][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:27][CH:28]=1)=[CH:10][CH:9]=2)=[O:4]

Participants

3

Reactant 2

HCID 27343144-Benzyloxy-phenylboronic acidHCID 866494596-bromo-4-hydroxy-2-oxo-2H-chromene-3-carboxylic acid methyl ester

Product 1

HCID 866494626-(4-Benzyloxy-phenyl)-4-hydroxy-2-oxo-2H-chromene-3-carboxylic acid methyl ester

Procedure

6-(4-Benzyloxy-phenyl)-4-hydroxy-2-oxo-2H-chromene-3-carboxylic acid methyl ester was prepared from 6-bromo-4-hydroxy-2-oxo-2H-chromene-3-carboxylic acid methyl ester (example 2-b) and 4-benzyloxyphenylboronic acid under conditions analogous to example 3-a. 1H NMR (200 MHz, CDCl3): δ (ppm)=8.14 (d, J=2.3 Hz, 1H), 7.85 (dd, J=8.5, 2.3 Hz, 1H), 7.54-7.08 (m, 10H), 5.12 (s, 2H), 4.04 (s, 3H).

Sources & evidence

ORD record
ord-407cf56d9ee44c4c8b2e706cba2cd19d
Source dataset
uspto-grants-2012_12
Patent number
US08324405B2

Reaction notes

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