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

HRID 1919511ノート

反応式

HRID 1919511 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9b571283749b408aa76744aecb83cfbb
出典データセット
uspto-grants-2012_05
特許番号
US08168635B2

反応ノート

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