Phosphorus tribromide → 2-(Bromomethyl)-3-methylnaphthalene

HRID 330260ノート

反応式

HRID 330260 の反応式
O[CH2:2][C:3]1[C:12]([CH3:13])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.P(Br)(Br)[Br:15]>CCOCC>[Br:15][CH2:2][C:3]1[C:12]([CH3:13])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1

参加物

4

反応物 2

HCID 24614Phosphorus tribromideHCID 14699377(3-Methylnaphthalen-2-yl)methanol

生成物 1

HCID 27530932-(Bromomethyl)-3-methylnaphthalene収率 87%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of 2-hydroxymethyl-3-methylnaphthalene (2.47 g, 14.4 mmol) in dry Et2O (50 mL) cooled to 0° C. was added phosphorus tribromide (4.88 g, 18 mmol) dropwise over 20 minutes. The resulting heterogeneous mixture was stirred at 0° C. for 1.25 hours and then quenched with H2O (50 mL). The reaction mixture was diluted further with H2O (50 mL) and extracted with Et1O (2×150 mL). The combined organic layers were washed with H2O (1×100 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by filtration through silica gel using CH2Cl2 as eluent to give the product as an off-white solid (2.94 g, 87%).

後処理

  1. customquenched with H2O (50 mL)
  2. additionThe reaction mixture was diluted further with H2O (50 mL)
  3. extractionextracted with Et1O (2×150 mL)
  4. washThe combined organic layers were washed with H2O (1×100 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. filtrationThe residue was purified by filtration through silica gel

出典と根拠

ORDレコード
ord-e3665f25a8c745bc8ecceaddb9d5c14c
出典データセット
uspto-grants-1990_01
特許番号
US04895861

反応ノート

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