Dichloromethane → Methanone, (4-methoxyphenyl)(2-phenyl-3-benzofuranyl)-

HRID 268339Notes

Reaction equation

HRID 268339 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.[C:16](Cl)(=[O:25])[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1.C(Cl)Cl>O>[CH3:24][O:23][C:20]1[CH:21]=[CH:22][C:17]([C:16]([C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[O:8][C:7]=2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:25])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7477p-Anisoyl chlorideHCID 35179362-Phenyl-benzofuran

Product 1

HCID 6613416Methanone, (4-methoxyphenyl)(2-phenyl-3-benzofuranyl)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a cooled (ice bath) mixture of 7.81 g. (0.040 mol.) of 2-phenylbenzofuran and 7.0 g. (0.041 mol.) of p-anisoyl 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-(4-methoxybenzoyl)-2-phenylbenzofuran.

Workup

  1. temperatureTo a cooled
  2. addition(ice bath) mixture of 7.81 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-0a91648082e94bb481ce8d6bb7491b35
Source dataset
uspto-grants-1976_03
Patent number
US03947470

Reaction notes

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