Triphenylphosphine → 3-Bromo-4-(3-methoxy-benzyloxy)-5-nitro-benzaldehyde

HRID 1663362

Reaction equation

HRID 1663362 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[OH:10])[CH:5]=[O:6].[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH2:19]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[O:10][CH2:19][C:18]1[CH:21]=[CH:22][CH:23]=[C:16]([O:15][CH3:14])[CH:17]=1)[CH:5]=[O:6]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 814373-Methoxybenzyl alcoholHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 14943783-Bromo-4-hydroxy-5-nitrobenzaldehyde

Product 1

HCID 866251583-Bromo-4-(3-methoxy-benzyloxy)-5-nitro-benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-bromo-4-hydroxy-5-nitro-benzaldehyde (87.4 mg) in dry dichloromethane (7.5 ml) was added 3-methoxybenzyl alcohol (35 μl), triphenylphosphine (103 mg) and diethyl azodicarboxylate (45 μl). The mixture was stirred under a nitrogen atmosphere for 17 h and then concentrated in vacuo. The residue was purified by chromatography on silicagel in heptane/ethyl acetate 9/1→1/1 (v/v) as eluent.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by chromatography on silicagel in heptane/ethyl acetate 9/1→1/1 (v/v) as eluent

Sources & evidence

ORD record
ord-8058568de9b44bb98faec1b0d7f1cddd
Source dataset
uspto-grants-2011_10
Patent number
US08034945B2

Linked notes

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