Bromine → 2-Bromo-3-(3,4,5-trimethoxybenzoyl)-6-methoxybenzofuran

HRID 1042588Notes

Reaction equation

HRID 1042588 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 247872422-Bromo-3-(3,4,5-trimethoxybenzoyl)-6-methoxybenzofuran

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-9a8ab322622343c19cca7b38daff871e
Source dataset
uspto-grants-2013_10
Patent number
US08557982B2

Reaction notes

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