Triphenylphosphine → 4-Bromo-1-(bromomethyl)-2-methylbenzene

HRID 24235ノート

反応式

HRID 24235 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]O)=[C:4]([CH3:10])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:30]N1C(=O)CCC1=O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:30])=[C:4]([CH3:10])[CH:3]=1

参加物

5

反応物 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 22280088(4-Bromo-2-methylphenyl)methanol2 回

生成物 1

HCID 225690184-Bromo-1-(bromomethyl)-2-methylbenzene

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

A solution of (4-bromo-2-methyl-phenyl)-methanol (Intermediate 133, 319.0 mg, 1.58 mmol) and triphenylphosphine (466.0 mg, 1.74 mmol) in 5 mL CH2Cl2 was cooled to 0° C. and N-bromosuccinimide (309.0 mg, 1.74 mmol) was added in 5 portions over 20 minutes. The solution was warmed to 25° C. and stirred for 17 hours. The reaction was quenched by the addition of dilute aqueous NaHCO3. The resulting mixture was extracted with Et2O and the combined organic layers were washed with H2O and saturated aqueous NaCl before being dried (Na2SO4) and concentrated under reduced pressure. The title compound, 350.0 mg (84%), was isolated by column chromatography (2-3% EtOAc—hexanes) as a colorless oil.

後処理

  1. customThe reaction was quenched by the addition of dilute aqueous NaHCO3
  2. extractionThe resulting mixture was extracted with Et2O
  3. washthe combined organic layers were washed with H2O and saturated aqueous NaCl
  4. dry with materialbefore being dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-94d01f7c4d004a3eb47ac9a70849725a
出典データセット
uspto-grants-2005_02
特許番号
US06855512B2

反応ノート

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