Carbon tetrabromide → HCID 67468969、化合物

HRID 1019745ノート

反応式

HRID 1019745 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[CH2:13][CH2:14]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:36]>C(Cl)Cl>[Br:36][CH2:14][CH2:13][C:3]1[CH:4]=[C:5]([O:11][CH3:12])[C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[Cl:1]

参加物

5

反応物 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 67469173HCID 67469173、化合物

生成物 1

HCID 67468969HCID 67468969、化合物収率 83.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-(2-chloro-5-methoxy-4-nitrophenyl)ethanol (0.85 g, 3.67 mmol) in DCM (20 mL), triphenylphosphine (1.54 g, 5.9 mmol) and carbon tetrabromide (1.46 g, 4.4 mmol) were added. The reaction mixture was maintained for 7 hours at room temperature then partitioned between water (50 mL) and EtOAc (80 mL). The separated aqueous phase was extracted with EtOAc (80 mL), then the combined organic extracts were dried (Na2SO4) and concentrated under reduced pressure. The product was purified by column chromatography on neutral silica gel using 5-15% EtOAc in hexane to give the title compound (0.9 g, 83%) as a solid.

後処理

  1. customthen partitioned between water (50 mL) and EtOAc (80 mL)
  2. extractionThe separated aqueous phase was extracted with EtOAc (80 mL)
  3. dry with materialthe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe product was purified by column chromatography on neutral silica gel using 5-15% EtOAc in hexane

出典と根拠

ORDレコード
ord-d0c6058e8f034612b58bc041950cde22
出典データセット
uspto-grants-2014_05
特許番号
US08716287B2

反応ノート

読み込み中…