N-bromobutanimide → 2-(Bromomethyl)-5-(2'-methoxy-5'-fluorobenzyl)tetrahydrofuran

HRID 1919511노트

반응식

HRID 1919511 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[CH2:10][CH:11]([OH:16])[CH2:12][CH2:13][CH:14]=[CH2:15].[Br:17]N1C(=O)CCC1=O>C(Cl)Cl>[Br:17][CH2:15][CH:14]1[CH2:13][CH2:12][CH:11]([CH2:10][C:4]2[CH:5]=[C:6]([F:9])[CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[O:16]1

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 674994761-(2'-Methoxy-5'-fluorophenyl)hex-5-en-2-ol

생성물 1

HCID 674990602-(Bromomethyl)-5-(2'-methoxy-5'-fluorobenzyl)tetrahydrofuran

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 1-(2′-methoxy-5′-fluorophenyl)hex-5-en-2-ol (1.35 g, 6.0 mmol) in dry CH2Cl2 (30 mL) at 0° C. was added N-bromosuccinimide (NBS, 1.30 g, 7.2 mmol) portionwise and the reaction was warmed to room temperature for 12 h. Solvent was then removed in vacuo and the residue was purified by flash column chromatography (5% EtOAc in Hexane, Rf=0.12) to give in the trans isomer (663 mg, 36%) as an oil.

후처리

  1. customSolvent was then removed in vacuo
  2. customthe residue was purified by flash column chromatography (5% EtOAc in Hexane, Rf=0.12)
  3. customto give in the trans isomer (663 mg, 36%) as an oil

출처 및 근거

ORD 기록
ord-9b571283749b408aa76744aecb83cfbb
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08168635B2

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