3-Benzyloxy-phenylboronic acid → HCID 23062364, compound

HRID 2109391Notes

Reaction equation

Br[C:2]1[C:6](Br)=[CH:5][O:4][C:3]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[CH2:13]([O:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH2:13]([O:20][C:21]1[CH:22]=[C:23]([C:2]2[C:6]([C:23]3[CH:24]=[CH:25][CH:26]=[C:21]([O:20][CH2:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:22]=3)=[CH:5][O:4][C:3]=2[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:24]=[CH:25][CH:26]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Reactant 2

HCID 27343133-Benzyloxy-phenylboronic acid

HCID 3713161HCID 3713161, compound

Product 1

HCID 23062364HCID 23062364, compoundYield 13.1%

Procedure

A reaction and treatment was carried out in the same manner as in Reference Example 5(1) using ethyl 3,4-dibromo-2-furancarboxylate (2.00 g) and 3-benzyloxyphenylboronic acid (1.80 g). The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/20), thereby giving 1.70 g of a mixture of ethyl 3-(3-benzyloxyphenyl)-4-bromo-2-furancarboxylate and ethyl 4-(3-benzyloxyphenyl)-3-bromo-2-furancarboxylate and 0.26 g of ethyl 3,4-bis(3-benzyloxyphenyl)-2-furancarboxylate.

Workup

customA reaction and treatment
customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/20)

Sources & evidence

ORD record: ord-d1d161a80de647d9a405608e4e896474
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07514452B2

Reaction notes

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