Butyl bromide → Butyl 4-bromo-3-(butyloxy)benzoate

HRID 404337노트

반응식

HRID 404337 반응식
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[OH:11].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:19][CH2:20][CH2:21][CH3:22]>CN(C=O)C.O>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:19][CH2:20][CH2:21][CH3:22])=[O:7])=[CH:4][C:3]=1[O:11][CH2:10][CH2:2][CH2:3][CH3:4]

참가 물질

6

반응물 3

HCID 8002Butyl bromideHCID 10796Cesium carbonateHCID 64209734-Bromo-3-hydroxybenzoic acid

생성물 1

HCID 57467609Butyl 4-bromo-3-(butyloxy)benzoate수율 66.81%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a flask containing 4-bromo-3-hydroxybenzoic acid (T9.1)(available from Combi-Blocks Inc.)(2.40 g, 11.06 mmol) and Cs2CO3 (8.287 g, 25.44 mmol) in DMF (40 mL), was added 1-bromobutane (2.494 mL, 23.22 mmol), and the mixture was stirred overnight. The reaction was diluted with water and extracted with EtOAc. The organic layers were washed with brine, dried over Na2SO4, filtered, concentrated, and then purified by CombiFlash® column chromatography (0 to 20% EtOAc/Hexanes) to provide T9.2 (2.4326 g, 66.81% yield).

후처리

  1. extractionextracted with EtOAc
  2. washThe organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by CombiFlash® column chromatography (0 to 20% EtOAc/Hexanes)
  7. customto provide T9.2 (2.4326 g, 66.81% yield)

출처 및 근거

ORD 기록
ord-b5cbdbc1d1ae4813b0734e182c02f7b1
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748462B2

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