Triphenylphosphine → 1-{[(2-Bromoethyl)oxy]methyl}-4-(1,1-dimethylethyl)benzene

HRID 1875663ノート

反応式

HRID 1875663 の反応式
[Br:1]N1C(=O)CCC1=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:28][C:29]([C:32]1[CH:37]=[CH:36][C:35]([CH2:38][O:39][CH2:40][CH2:41]O)=[CH:34][CH:33]=1)([CH3:31])[CH3:30]>C(Cl)Cl.[Al]>[Br:1][CH2:41][CH2:40][O:39][CH2:38][C:35]1[CH:36]=[CH:37][C:32]([C:29]([CH3:31])([CH3:30])[CH3:28])=[CH:33][CH:34]=1

参加物

6

反応物 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 104885912-({[4-(1,1-Dimethylethyl)phenyl]methyl}oxy)ethanol

生成物 1

HCID 136543781-{[(2-Bromoethyl)oxy]methyl}-4-(1,1-dimethylethyl)benzene収率 12%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒4 回HCID 5359268Aluminum溶媒

実験手順

A solution of N-bromosuccinimide (272 mg, 1.53 mmol) in DCM (2.5 mL) was added to resin-bound triphenylphosphine (510 mg, 1.53 mEquiv, Fluka) in DCM (2.5 mL), and the reaction was stirred at rt for 10 min. A solution of 2-({[4-(1,1-dimethylethyl)phenyl]methyl}oxy)ethanol (160 mg, 0.768 mmol) in DCM (1.5 mL) was added to the reaction, and the residual alcohol was transferred with additional DCM (1.5 mL). The reaction vial was capped, wrapped in aluminum foil, and stirred at rt for 20 h. The reaction was filtered through a SPE cartridge (5 g silica) eluting with the following 10 mL fractions: DCM (fraction 1), 30% EtOAc/hexanes (fraction 2), and 50% EtOAc/hexanes (fraction 3) to give the title compound (25 mg, 12%). The product was characterized by 1H NMR (400 MHz) in CDCl3.

後処理

  1. customThe reaction vial was capped
  2. stirringstirred at rt for 20 h
  3. filtrationThe reaction was filtered through a SPE cartridge (5 g silica)
  4. washeluting with the following 10 mL fractions

出典と根拠

ORDレコード
ord-995770c1a637475189d090889b75f588
出典データセット
uspto-grants-2012_11
特許番号
US08309572B2

反応ノート

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