Phosphorus oxybromide → 4-Bromo-1-(bromomethyl)-2-(methylsulfonyl)benzene

HRID 1406312ノート

反応式

HRID 1406312 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]O)=[C:4]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:3]=1.P(Br)(Br)([Br:16])=O.P(Br)(Br)Br>[Cl-].[Na+].O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:16])=[C:4]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:3]=1

参加物

5

反応物 3

HCID 24613Phosphorus oxybromideHCID 24614Phosphorus tribromideHCID 59251623[4-Bromo-2-(methanesulfonyl)phenyl]methanol

生成物 1

HCID 27610744-Bromo-1-(bromomethyl)-2-(methylsulfonyl)benzene収率 160.5%

試薬・触媒・溶媒 1

HCID 57417360Sodium chloride; water溶媒

反応条件

温度
130 °C

実験手順

To a solution of (4-bromo-2-methanesulfonyl-phenyl)-methanol (preparation 112) (100 mg, 0.38 mmol) in POBr3 (542 mg, 1.89 mmol) was added PBr3 (511 mg, 1.89 mmol). After the addition, the reaction mixture was stirred at 130° C. overnight. TLC (petroleum ether:EtOAc 1:1) showed the reaction was complete. The reaction was cooled to room temperature and then poured into brine (10 mL) and extracted with EtOAc (10 mL×2). The combined organic layers were washed with brine (10 mL×2), dried over sodium sulfate and concentrated in vacuo to give crude 4-bromo-1-bromomethyl-2-methanesulfonyl-benzene (200 mg, 80%) as a white solid.

後処理

  1. additionAfter the addition
  2. temperatureThe reaction was cooled to room temperature
  3. extractionextracted with EtOAc (10 mL×2)
  4. washThe combined organic layers were washed with brine (10 mL×2)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-0a6ca641ef8647719cfa6bd1eb36e776
出典データセット
uspto-grants-2014_12
特許番号
US08916593B2

反応ノート

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