Carbon tetrabromide → HCID 67468969、化合物

HRID 1019759ノート

反応式

HRID 1019759 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 90%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 2-(2-chloro-5-methoxy-4-nitrophenyl)ethanol (7.0 g, 30.22 mmol), triphenylphosphine (12.68 g, 48.3 mmol) and carbon tetrabromide (14.03 g, 42.3 mmol) in DCM (150 mL) was stirred at room temperature for 2 hours. The mixture was partitioned between water (150 mL) and EtOAc (100 mL), and then the separated aqueous phase was extracted with EtOAc (100 mL). The combined organic extracts were washed with water (80 mL), brine (80 mL), dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by column chromatography on neutral silica gel using 0-1% methanol in DCM to give the title compound (8.0 g, 90%) as a solid.

後処理

  1. customThe mixture was partitioned between water (150 mL) and EtOAc (100 mL)
  2. extractionthe separated aqueous phase was extracted with EtOAc (100 mL)
  3. washThe combined organic extracts were washed with water (80 mL), brine (80 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography on neutral silica gel using 0-1% methanol in DCM

出典と根拠

ORDレコード
ord-a69b0bc378644f0381fadba5a9476ad4
出典データセット
uspto-grants-2014_05
特許番号
US08716287B2

反応ノート

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