Allyl bromide → 4-(Allyloxy)-5-bromo-2-chlorobenzonitrile

HRID 2206693

반응식

HRID 2206693 반응식
[Br:1][C:2]1[C:3]([OH:11])=[CH:4][C:5]([Cl:10])=[C:6]([CH:9]=1)[C:7]#[N:8].[CH2:12](Br)[CH:13]=[CH2:14].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:14]([O:11][C:3]1[C:2]([Br:1])=[CH:9][C:6]([C:7]#[N:8])=[C:5]([Cl:10])[CH:4]=1)[CH:13]=[CH2:12]

참가 물질

5

반응물 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 533304525-Bromo-2-chloro-4-hydroxybenzonitrile

생성물 1

HCID 867140364-(Allyloxy)-5-bromo-2-chlorobenzonitrile수율 65%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A mixture of compound 37 (20.5 g, 88.1 mmol), allyl bromide (11.2 mL, 132 mmol) and K2CO3 (24.4 g, 176 mmol) in acetone (440 mL) was stirred for 3 hours under reflux. The mixture was filtrated and concentrated in vacuo. The resultant was partitioned between EtOAc and water. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to afford the product 38 (15.6 g, 65%) as a white solid.

후처리

  1. temperatureunder reflux
  2. filtrationThe mixture was filtrated
  3. concentrationconcentrated in vacuo
  4. customThe resultant was partitioned between EtOAc and water
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-bdbbee18eaab4fd48597365336264816
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09371303B2

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