Hydrochloric Acid → (4-Bromo-2-methoxyphenyl)(4-fluorophenyl)methanone

HRID 2116635

反応式

HRID 2116635 の反応式
[Al+3].[Cl-].[Cl-].[Cl-].[F:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][CH:7]=1.[Br:15][C:16]1[CH:17]=[C:18]([O:22][CH3:23])[CH:19]=[CH:20][CH:21]=1.Cl>ClCCCl>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([C:10]([C:9]2[CH:13]=[CH:14][C:6]([F:5])=[CH:7][CH:8]=2)=[O:11])=[C:18]([O:22][CH3:23])[CH:17]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 169713-BromoanisoleHCID 678794-Fluorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 59814869(4-Bromo-2-methoxyphenyl)(4-fluorophenyl)methanone収率 18.3%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒2 回

実験手順

To a suspension of AlCl3 (14.7 g, 110 mmol) in 250 mL of 1,2-dichloroethane was added 4-fluorobenzoyl chloride (11.8 mL, 100 mmol) at rt. The resulting mixture was stirred at rt for 15 min. and 3-bromoanisole (16.8 g, 90.0 mmol) in 20 mL of 1,2-dichloroethane was added. After 1 h at rt, the brown solution was poured into ice. 2N HCl was added to the aqueous layer followed by an extraction with CH2Cl2. The combined organics were dried (MgSO4), filtered and concentrated. The residue was subjected to chromatography on silica gel (EtOAc/hexane 5:95 to 7:93) affording 5.1 g of a solid that was triturated with 20 mL of EtOAc/hexane (10:90). The title compound was obtained from filtration, and additional product was recovered from the mother liquors.

後処理

  1. waitAfter 1 h at rt
  2. additionthe brown solution was poured into ice
  3. extractionfollowed by an extraction with CH2Cl2
  4. dry with materialThe combined organics were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-bc439dbf08e24a499e1b74945d71ca24
出典データセット
uspto-grants-2008_10
特許番号
US07439260B2

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