3-Nitrophenylboronic Acid → Methyl 3-(3-nitrophenyl)benzoate

HRID 1069069Notes

Reaction equation

HRID 1069069 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[N+:12]([C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1)([O-:14])=[O:13]>C1C=CC([P]([Pd]([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)=CC=1>[CH3:8][O:7][C:5]([C:4]1[CH:3]=[C:2]([C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:12]([O-:14])=[O:13])[CH:20]=2)[CH:11]=[CH:10][CH:9]=1)=[O:6]

Participants

4

Reactant 2

HCID 16773-Nitrophenylboronic AcidHCID 12070Methyl 3-bromobenzoate

Product 1

HCID 11708671Methyl 3-(3-nitrophenyl)benzoate

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

n.m.r. δ values include 3.96 (s, 3 H), 7.57 (t, 1 H), 7.64 (t, 1 H), 7.81 (d, 1 H), 7.94 (d,1 H), 8.09 (d, 1 H), 8.23 (dd, 1 H), 8.30 (s, 1 H), 8.48 (t, 1 H), m.p., 88-90° C.; from methyl 3-bromobenzoate (2.0 g), tetrakis(triphenylphosphine)palladium(0) (348mg) and 3-nitrophenylboronic acid (1.9 g).

Workup

  1. customm.p., 88-90° C.

Sources & evidence

ORD record
ord-7ecbcf7ca684446b868c276e99af2223
Source dataset
uspto-grants-2001_06
Patent number
US06251925B1

Reaction notes

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