2-Bromophenol → (E)-3-(2-bromo-phenoxy)-but-2-enoic acid ethyl ester

HRID 19149

반응식

HRID 19149 반응식
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[CH2:9]([O:11][C:12](=[O:16])[C:13]#[C:14][CH3:15])[CH3:10].N12CCCN=C1CCCCC2>O1CCCC1>[CH2:9]([O:11][C:12](=[O:16])/[CH:13]=[C:14](/[O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1])\[CH3:15])[CH3:10]

참가 물질

5

반응물 3

HCID 72442-BromophenolHCID 78043Ethyl 2-butynoateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

생성물 1

HCID 66894257(E)-3-(2-bromo-phenoxy)-but-2-enoic acid ethyl ester수율 67.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a stirred mixture of 2-bromo-phenol (9.02 g, 0.052 mol) and ethyl-2-butynoate (11.7 g, 0.104 mol) in tetrahydrofuran (50 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (8.05 g, 0.053 mol) slowly. After addition was complete the mixture was stirred at reflux overnight. Upon completion of the reaction the tetrahydrofuran was removed in vacuo and the residue was diluted in diethyl ether and washed first with 1N aqueous hydrochloric acid, then 10% aqueous sodium hydroxide solution, a saturated sodium chloride solution and dried over magnesium sulfate. The mixture was filtered and evaporated and the residue dried under high vacuum which afforded (E)-3-(2-bromo-phenoxy)-but-2-enoic acid ethyl ester as a yellow oil (10.0 g, 67%) and used without further purification.

후처리

  1. additionAfter addition
  2. temperatureat reflux overnight
  3. customwas removed in vacuo
  4. additionthe residue was diluted in diethyl ether
  5. washwashed first with 1N aqueous hydrochloric acid
  6. dry with material10% aqueous sodium hydroxide solution, a saturated sodium chloride solution and dried over magnesium sulfate
  7. filtrationThe mixture was filtered
  8. customevaporated
  9. customthe residue dried under high vacuum which

출처 및 근거

ORD 기록
ord-949881276d1f48c8bcdcc1a425e5f0fa
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741327B2

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