Dimethyl Sulfate → (6-Bromo-3-methoxybenzofuran2-yl)(2,4-dichloro-phenyl)methanone

HRID 29252Notes

Reaction equation

HRID 29252 reaction equation
[Br:1][C:2]1[CH:21]=[CH:20][C:5]2[C:6](=[O:19])[CH:7]([C:9](=[O:18])[C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=3[Cl:17])[O:8][C:4]=2[CH:3]=1.S(OC)(O[CH3:26])(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[Br:1][C:2]1[CH:21]=[CH:20][C:5]2[C:6]([O:19][CH3:26])=[C:7]([C:9]([C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=3[Cl:17])=[O:18])[O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 10796Cesium carbonateHCID 597888916-Bromo-2-(2,4-dichloro-benzoyl)-benzofuran-3-one

Product 1

HCID 59788953(6-Bromo-3-methoxybenzofuran2-yl)(2,4-dichloro-phenyl)methanoneYield 28%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 6-Bromo-2-(2,4-dichloro-benzoyl)-benzofuran-3-one (3.30 g, 8.55 mmol) in acetone (50 mL) was added dimethyl sulfate (1.19 g, 9.40 mmol) and cesium carbonate (4.18 g, 12.82 mmol). The resulting mixture was heated at 50 deg for 6 hours at which time the reaction mixture was concentrated via rotary evaporation. The resulting mixture was taken up in EtOAc and washed twice with water and one time with a saturated sodium carbonate solution. The organic portion was dried over MgSO4 and then filtered and concentrated. The resultant oil was purified via column chromatography (10% MeOH/Dichloromethane) to provide the title compound (950 mg, 28%). 1H-NMR (CDCl3): δ 8.03 (d, 1H), 7.65 (d, 1H), 7.46 (m, 2H), 7.35 (m, 2H), 2.46 (s, 3H).

Workup

  1. temperatureThe resulting mixture was heated at 50 deg for 6 hours at which time the reaction mixture
  2. concentrationwas concentrated via rotary evaporation
  3. washwashed twice with water and one time with a saturated sodium carbonate solution
  4. dry with materialThe organic portion was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resultant oil was purified via column chromatography (10% MeOH/Dichloromethane)

Sources & evidence

ORD record
ord-d27857088dd442ceb3948ffac8f3ee15
Source dataset
uspto-grants-2008_09
Patent number
US07420066B2

Reaction notes

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