Benzene, 4-bromo-1,2-dimethoxy- → HCID 19754904, compound

HRID 1588905Notes

Reaction equation

HRID 1588905 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:10][CH3:11])[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.C([Li])CCC.[CH:17]1([N:22]([CH:33]2[CH2:37][CH2:36][CH2:35][CH2:34]2)[C:23](=[O:32])[C:24]2[CH:31]=[CH:30][C:27]([CH:28]=[O:29])=[CH:26][CH:25]=2)[CH2:21][CH2:20][CH2:19][CH2:18]1>>[CH:17]1([N:22]([CH:33]2[CH2:37][CH2:36][CH2:35][CH2:34]2)[C:23](=[O:32])[C:24]2[CH:31]=[CH:30][C:27]([CH:28]([C:2]3[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH3:11])[CH:3]=3)[OH:29])=[CH:26][CH:25]=2)[CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

4

Reactant 3

HCID 76114Benzene, 4-bromo-1,2-dimethoxy-HCID 53771725HCID 53771725, compoundHCID 178418339Butyllithium

Product 1

HCID 19754904HCID 19754904, compound

Procedure

The reaction and workup were carried out in the same manner as described in Example 8 using 4-bromoveratrole (1.29 mL, 10 mmol), n-butyl lithium (6.25 mL of 1.6 M solution in hexane), terephthalaldehydic acid N,N-dicyclopentyl amide (Example 29) (2.6 g, 9.1 mmol). The crude product was chromatographed on silica gel using mixtures of ethyl acetate and hexane to give the title compound as an oil that crystallized under ethyl ether: m. pt. 137-138° C.

Workup

  1. customThe reaction and workup
  2. customThe crude product was chromatographed on silica gel using mixtures of ethyl acetate and hexane

Sources & evidence

ORD record
ord-0e2ecdc375124ae1a482faf93a34cf0e
Source dataset
uspto-grants-1993_06
Patent number
US05223539

Reaction notes

Loading…