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Azobisisobutyronitrile → 4-(bromomethyl)-5-chloro-2-fluoro-N-(methylsulfonyl)benzamide

HRID 1849588
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HRID 1849588 반응식
[Cl:1][C:2]1[C:3]([CH3:16])=[CH:4][C:5]([F:15])=[C:6]([CH:14]=1)[C:7]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[O:8].[Br:17]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>ClCCCl>[Br:17][CH2:16][C:3]1[C:2]([Cl:1])=[CH:14][C:6]([C:7]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[O:8])=[C:5]([F:15])[CH:4]=1
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5

반응물 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 580423685-Chloro-2-fluoro-4-methyl-N-(methylsulfonyl)benzamide

생성물 1

HCID 580423974-(bromomethyl)-5-chloro-2-fluoro-N-(methylsulfonyl)benzamide

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

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온도
90 °C

실험 절차

A mixture of 5-chloro-2-fluoro-4-methyl-N-(methylsulfonyl)benzamide (0.8 g, 3.0 mmol), N-bromosuccinimide (1.6 g, 9.0 mmol) and azodiisobutyronitrile (16 mg, 0.09 mmol) in 1,2-dichloroethane (20 mL) was stirred at 90° C. for 16 hrs. The reaction was quenched with Na2SO3 (10 mL, 10%), extracted with 1,2-dichloroethane (20 mL×3), dried over anhydrous Na2SO4, concentrated and the residue was used in next step without further purification (1.1 g, crude). LCMS (ESI) m/z: 342.0 [M+H]+.

후처리

  1. customThe reaction was quenched with Na2SO3 (10 mL, 10%)
  2. extractionextracted with 1,2-dichloroethane (20 mL×3)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customthe residue was used in next step without further purification (1.1 g, crude)

출처 및 근거

ORD 기록
ord-e78b229000e24ba2bc19933ebdf50bc1
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08952169B2

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