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

HRID 529234Notes

Reaction equation

HRID 529234 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)methanoneYield 37.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred solution of 2-t-butyldimethylsilyl-3-(3,4,5-trimethoxybenzoyl)-6-methoxybenzofuran (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 thiosulfate solution, extracted with ethyl acetate (20 mL), dried over magnesium sulfate 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 thiosulfate solution
  2. extractionextracted with ethyl acetate (20 mL)
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent removed by distillation under vacuum
  5. customThe crude product was re-crystallised from acetonitrile

Sources & evidence

ORD record
ord-13059b83e7ee4032806fbd9f33124e39
Source dataset
uspto-grants-2016_05
Patent number
US09346842B2

Reaction notes

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