N-bromobutanimide → Methyl 12-bromo-11-dodecynoate

HRID 1024536노트

반응식

HRID 1024536 반응식
[C:1]([O:14][CH3:15])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]#[CH:12].[Br:16]N1C(=O)CCC1=O>CC(C)=O.[N+]([O-])([O-])=O.[Ag+]>[Br:16][C:12]#[C:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([O:14][CH3:15])=[O:13]

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 28971611-Dodecynoic acid, methyl ester

생성물 1

HCID 86668474Methyl 12-bromo-11-dodecynoate수율 94%

시약·촉매·용매 2

HCID 24470Silver Nitrate촉매HCID 180Acetone용매

실험 절차

To a mechanically stirred solution of ester 4 (37 g, 176 mmol) in 700 mL of acetone under nitrogen was added N-bromosuccinimide (34.4 g, 194 mmol) followed by silver nitrate (2.7 g, 18 mmol). The reaction mixture was allowed to stir at room temperature in the absence of light for 21 h. The thick, pale yellow reaction mixture was filtered through a sintered glass funnel, concentrated in vacuo to one third volume, and diluted with 500 mL of water. This was extracted with 4×250 mL of hexanes, and the combined organic layers were washed with 100 mL of brine, dried over sodium sulfate, concentrated in vacuo, and vacuum dried to give bromoacetylene 5 (47.81 g, 94%) as a yellow oil:

후처리

  1. filtrationThe thick, pale yellow reaction mixture was filtered through a sintered glass funnel
  2. concentrationconcentrated in vacuo to one third volume
  3. additiondiluted with 500 mL of water
  4. extractionThis was extracted with 4×250 mL of hexanes
  5. washthe combined organic layers were washed with 100 mL of brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo, and vacuum
  8. customdried

출처 및 근거

ORD 기록
ord-07dabd8093a74d8d8ec04b144bf62099
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722910B2

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