3-Nitrophenylboronic Acid → 3'-Nitro-[1,1'-biphenyl]-3,4-dicarboxylic acid dimethyl ester

HRID 1069071Notes

Reaction equation

HRID 1069071 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[C:5](=[CH:10][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7].[N+:16]([C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1)([O-:18])=[O:17]>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>[CH3:15][O:14][C:12]([C:4]1[CH:3]=[C:2]([C:23]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:16]([O-:18])=[O:17])[CH:24]=2)[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])=[O:13]

Participants

4

Reactant 2

HCID 16773-Nitrophenylboronic AcidHCID 113232621,2-Dimethyl 4-bromobenzene-1,2-dicarboxylate

Product 1

HCID 544941873'-Nitro-[1,1'-biphenyl]-3,4-dicarboxylic acid dimethyl ester

Reagents, catalysts & solvents 1

HCID 178420553HCID 178420553, compoundCatalyst

Procedure

n.m.r. δ values include 3.93 (s, 3 H), 3.94 (s, 3 H), 7.65 (t, 1 H), 7.78 (dd, 1 H), 7.86 (d, 1 H), 7.92-7.95 (m, 2 H), 8.26 (dd, 1 H), 8.46 (t, 1 H); from dimethyl 4-bromophthalate (1.80 g), tetrakis(triphenylphosphino)palladium(0) (246 mg) and 3-nitrophenylboronic acid (1.3 g)

Sources & evidence

ORD record
ord-cec94691f3b644e9bd75da54b2117515
Source dataset
uspto-grants-2001_06
Patent number
US06251925B1

Reaction notes

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