Water → 4-(3-Bromophenyl)morpholine

HRID 351666

反応式

HRID 351666 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].Br[CH2:10][CH2:11][O:12][CH2:13][CH2:14]Br.C(N(C(C)C)CC)(C)C.O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([N:5]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1

参加物

6

反応物 4

HCID 962WaterHCID 115623-BromoanilineHCID 21521Bis(2-bromoethyl) etherHCID 81531Diisopropylethylamine

生成物 1

HCID 49612684-(3-Bromophenyl)morpholine収率 43%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

3-Bromoaniline (3.0 mL, 4.7 g, 28 mmol), 2-bromoethylether (4.2 mL, 7.7 g, 33 mmol) and diisopropylethylamine (15 mL, 11 g, 86 mmol) were dissolved in anhydrous DMF (20 mL) under inert gas atmosphere and heated to 100° C. for 6 h. After cooling to room temperature the mixture was poured into water (300 mL) and extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4), filtered and evaporated to dryness. Purification of the residue by flash chromatography afforded 2.9 g (12 mmol, 43% yield) of 4-(3-bromophenyl)morpholine.

後処理

  1. temperatureAfter cooling to room temperature the mixture
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customPurification of the residue by flash chromatography

出典と根拠

ORDレコード
ord-611775a44d3a4022a33695b08c5088f4
出典データセット
uspto-grants-2004_06
特許番号
US06743788B2

関連ノート

読み込み中…