Bromine → 5-Bromo-1,3-difluoro-2-(methylsulfanyl)benzene

HRID 748943ノート

反応式

HRID 748943 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[S:9][CH3:10].[Br:11]Br.[Cl-].[Al+3].[Cl-].[Cl-].S([O-])([O-])(=O)=S.[Na+].[Na+]>[Fe].C(OCC)C.ClCCl>[Br:11][C:6]1[CH:7]=[C:2]([F:1])[C:3]([S:9][CH3:10])=[C:4]([F:8])[CH:5]=1

参加物

8

反応物 4

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 6451240Aluminum(III) ChlorideHCID 132502621,3-Difluoro-2-(methylsulfanyl)benzene

生成物 1

HCID 235966125-Bromo-1,3-difluoro-2-(methylsulfanyl)benzene収率 17%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

Combine 1,3-difluoro-2-methylsulfanyl-benzene (4.3 g, 27 mmol), iron (300 mg, 5.4 mmol), bromine (1.4 mL, 27 mmol), aluminium chloride (400 mg, 3.0 mmol) and dichloromethane (100 mL), at 0° C. Stir the reaction mixture at room temperature for 2 hours. Add saturated sodium thiosulfate solution (20 mL) and diethyl ether (100 mL). Separate the layers and wash the organic layer with brine (20 mL). Dry with MgSO4, filter and concentrate in vacuo. Chromatograph the residue on a column eluting the material with diethyl ether in hexane (0 to 5%) to give 1.1 g of 5-bromo-1,3-difluoro-2-methylsulfanyl-benzene (17%).

後処理

  1. customat 0° C
  2. customSeparate the layers
  3. washwash the organic layer with brine (20 mL)
  4. dry with materialDry with MgSO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. washChromatograph the residue on a column eluting the material with diethyl ether in hexane (0 to 5%)

出典と根拠

ORDレコード
ord-82b15db61fb14abbbdc2815e516e50f6
出典データセット
uspto-grants-2008_07
特許番号
US07399867B2

反応ノート

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