Dichloromethane → 3-(3,5-Dimethyl-4-methoxybenzoyl)-2-phenylbenzofuran

HRID 268346Notes

Reaction equation

HRID 268346 reaction equation
[C:1]1([C:7]2[O:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([CH3:28])[C:25]=1[O:26][CH3:27])[C:20](Cl)=[O:21].C(Cl)Cl>O>[CH3:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([CH3:28])[C:25]=1[O:26][CH3:27])[C:20]([C:11]1[C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[O:8][C:7]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:21]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 35179362-Phenyl-benzofuranHCID 214353833,5-Dimethyl-4-methoxybenzoyl chloride

Product 1

HCID 214353583-(3,5-Dimethyl-4-methoxybenzoyl)-2-phenylbenzofuran

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a cooled (ice bath) mixture of 10.5 g. (0.054 mol.) of 2-phenylbenzofuran and 11.5 g. (0.058 mol.) of 3,5-dimethyl-4-methoxybenzoyl chloride in 100 ml. of methylene chloride is added dropwise 28.7 g. (0.11 mol.) of stannic chloride. The reaction mixture is allowed to warm to ambient temperature, then stirred for 2 hours. Water is slowly added to the mixture and it is stirred an additional 30 minutes. The layers are separated and the organic phase is washed with water until the washings are neutral, dried (MgSO4) and concentrated to give 3-(3,5-dimethyl-4-methoxybenzoyl)-2-phenylbenzofuran.

Workup

  1. temperatureTo a cooled
  2. addition(ice bath) mixture of 10.5 g
  3. stirringis stirred an additional 30 minutes
  4. customThe layers are separated
  5. washthe organic phase is washed with water until the washings
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4c3a1de1f0214919bba106ff5552f614
Source dataset
uspto-grants-1976_03
Patent number
US03947470

Reaction notes

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