Phosphorus tribromide → tert-Butyl 3-(1-bromoethyl)phenylcarbamate

HRID 2175259ノート

反応式

HRID 2175259 の反応式
O[CH:2]([C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:7]=[CH:8][CH:9]=1)[CH3:3].[Br:18]P(Br)Br>C(Cl)Cl.C1COCC1>[Br:18][CH:2]([C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:7]=[CH:8][CH:9]=1)[CH3:3]

参加物

5

反応物 2

HCID 24614Phosphorus tribromideHCID 16740724tert-butyl N-[3-(1-hydroxyethyl)phenyl]carbamate

生成物 1

HCID 86712586tert-Butyl 3-(1-bromoethyl)phenylcarbamate収率 78%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
5 °C

実験手順

To a solution of tert-butyl 3-(1-hydroxyethyl)phenylcarbamate (5.8 g, 24.44 mmol) in CH2Cl2 (30 mL) and THF (20 mL) at 0° C. was added tribromophosphine (1 M solution in CH2Cl2, 24.44 mL, 24.44 mmol). The reaction was stirred at 0-10° C. for 1.5 h and then quenched with water. The mixture was extracted with CH2Cl2. The organic layer was washed with saturated NaHCO3 and brine, dried over anhydrous MgSO4, filtered and concentrated to afford the title compound (5.7 g, 78% yield) as a colorless oil. LCMS, [M+Na]+=322.1.

後処理

  1. customquenched with water
  2. extractionThe mixture was extracted with CH2Cl2
  3. washThe organic layer was washed with saturated NaHCO3 and brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-64a6a54f2b4940b1847a406c162fb8b2
出典データセット
uspto-grants-2015_06
特許番号
US09062028B2

反応ノート

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