Bromine → 2-Bromo-7-acetoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxybenzofuran

HRID 2059629Notes

Reaction equation

HRID 2059629 reaction equation
[Si]([C:8]1[O:9][C:10]2[C:30]([O:31][C:32](=[O:34])[CH3:33])=[C:29]([O:35][CH3:36])[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:37]Br>ClCCCl>[Br:37][C:8]1[O:9][C:10]2[C:30]([O:31][C:32](=[O:34])[CH3:33])=[C:29]([O:35][CH3:36])[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 247865592-t-Butyldimethylsilyl-7-acetoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxybenzofuran

Product 1

HCID 247865602-Bromo-7-acetoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxybenzofuran

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred solution of 2-t-butyldimethylsilanyl-7-acetoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxy-benzofuran(120 mg, 0.44 mmol) in 1,2-dichloroethane (1 mL) at room temperature under nitrogen was added bromine (12 μl, 0.44 mmol) dropwise and the reaction mixture was stirred at this temperature 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 purified by silica gel column chromatography (eluent=Hexane:diethyl ether; 8:2-7:3) to afford the title compound as a colourless crystalline solid; (91 mg, 81%); 1H NMR (300 MHz, CDCl3) δ 7.40(d, 1H, J=8.70 Hz), 7.14(s, 2H, benzoyl-Hs), 6.98(d, 1H, J=8.75 Hz), 3.94(s, 3H, OMe), 3.89(s, 3H, OMe), 3.86(s, 6H, 2×OMe), 2.43(s, 3H); 13C NMR (75 MHz, CDCl3) δ 187.95(CO), 167.71, 152.75, 149.54, 147.49, 142.59, 131.92, 131.80, 123.91, 121.84, 119.89, 117.72, 109.89, 106.92, 60.69, 56.61, 56.00, 20.09.

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 purified by silica gel column chromatography (eluent=Hexane:diethyl ether; 8:2-7:3)

Sources & evidence

ORD record
ord-f7b04b12d4c34ec0b06e27d10dfa7696
Source dataset
uspto-grants-2012_10
Patent number
US08278290B2

Reaction notes

Loading…