Bromine → (2-Bromo-6-methoxy-3-benzofuranyl)(3,4,5-trimethoxyphenyl)methanone

HRID 2059624Notes

Reaction equation

HRID 2059624 reaction equation
[Si]([C:8]1[O:9][C:10]2[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:11]=2[C:12]=1[C:13](=[O:26])[C:14]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=1)(C(C)(C)C)(C)C.[Br:33]Br>ClCCCl>[Br:33][C:8]1[O:9][C:10]2[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:11]=2[C:12]=1[C:13](=[O:26])[C:14]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 247872412-t-Butyldimethylsilyl-3-(3,4,5-trimethoxybenzoyl)-6-methoxy-benzofuran

Product 1

HCID 24787242(2-Bromo-6-methoxy-3-benzofuranyl)(3,4,5-trimethoxyphenyl)methanone

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred solution of 2-t-butyldimethylsilanyl-3-(3,4,5-trimethoxybenzoyl)-6-methoxy-benzofuran (200 mg, 0.44 mmol) in 1,2-dichloroethane (2 mL) at 0° C. under nitrogen was added bromine (23 μl, 0.44 mmol) dropwise and the reaction mixture was stirred for 10 minutes. After this time the reaction was quenched with saturated sodium thiosulphate solution, extracted with ethyl acetate (20 mL), dried over magnesium sulphate and the solvent removed by distillation under vacuum. The crude product was re-crystallised from acetonitrile to afford the title compound as a colourless crystalline solid; (69 mg, 37%); 1H NMR (300 MHz, CDCl3) δ 7.45(d, 1H, J=8.78 Hz), 7.15(s, 2H, benzoyl-Hs), 7.01(d, 1H, J=2.18 Hz), 6.90(dd, 1H, J=8.74, 2.27 Hz), 3.94(s, 3H, OMe), 3.85(s, 9H, 3×OMe); 13C NMR (75 MHz, CDCl3) δ 188.21(CO), 158.29, 155.80, 152.72, 142.55, 131.99, 130.69, 120.98, 119.97, 119.67, 112.90, 107.00, 95.30, 60.67, 55.94, 55.43.

Workup

  1. customAfter this time the reaction was quenched with saturated sodium thiosulphate solution
  2. extractionextracted with ethyl acetate (20 mL)
  3. dry with materialdried over magnesium sulphate
  4. customthe solvent removed by distillation under vacuum
  5. customThe crude product was re-crystallised from acetonitrile

Sources & evidence

ORD record
ord-49b8e4e3e0c442fb8aaeb6ce6693879b
Source dataset
uspto-grants-2012_10
Patent number
US08278290B2

Reaction notes

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