3-Nitrophenylboronic Acid → 5-(3-Nitrophenyl)-2,3-dihydro-7-benzofurancarboxylic acid methyl ester

HRID 1069073Notes

Reaction equation

HRID 1069073 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[O:12][CH2:11][CH2:10][C:9]=2[CH:8]=[C:7](Br)[CH:6]=1)=[O:4].C(=O)([O-])[O-].[Na+].[Na+].[N+:21]([C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1)([O-:23])=[O:22]>CO.C1(P([Pd-4](P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[C:13]2[O:12][CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]([C:28]2[CH:27]=[CH:26][CH:25]=[C:24]([N+:21]([O-:23])=[O:22])[CH:29]=2)[CH:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 16773-Nitrophenylboronic AcidHCID 10340Sodium CarbonateHCID 54179230Methyl 5-bromo-2,3-dihydrobenzofuran-7-carboxylate

Product 1

HCID 545606555-(3-Nitrophenyl)-2,3-dihydro-7-benzofurancarboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 178420553HCID 178420553, compoundCatalystHCID 887MethanolSolvent

Procedure

m.p. 53-57 ° C.; from 5-bromo-2,3-dihydro-7-benzofurancarboxylic acid methyl ester (1.0 g), tetrakis(triphenylphosphino)palladium(0) (103 mg), 2 M sodium carbonate (7.0 mL) and 3-nitrophenylboronic acid (741 mg) in methanol (5 mL).

Sources & evidence

ORD record
ord-730182f123984940ad7f59cac7dbba00
Source dataset
uspto-grants-2001_06
Patent number
US06251925B1

Reaction notes

Loading…