Boron tribromide → 3-Chloro-4-methoxysalicylaldehyde

HRID 1154589ノート

反応式

HRID 1154589 の反応式
[Cl:1][C:2]1[C:3]([O:12]C)=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[C:3]([OH:12])=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6]

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 133437053-Chloro-2,4-dimethoxybenzaldehyde

生成物 1

HCID 133437063-Chloro-4-methoxysalicylaldehyde

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of 72.0 g. (0.359 mol) of (13h) in 450 ml. of CH2Cl2 at -50° C. under N2 was added dropwise 90.0 g. (0.359 mol) of BBr3. After the addition was complete, the reaction mixture was warmed to 0° C. and stirred for 1 hour. The reaction mixture was then poured into 500 ml. of ice-water and extracted with EtOAc. The organic solution was washed with aqueous NaCl and dried over Na2SO4. Evaporation of the EtOAc gave a residue that was rapidly passed through a silica gel column eluting with an EtOAc/CH2Cl2 mixture. This afforded 49.5 g. of (14h), m.p. 114°-117° C. Analysis (C8H7ClO3) C,H.

後処理

  1. additionAfter the addition
  2. additionThe reaction mixture was then poured into 500 ml
  3. extractionof ice-water and extracted with EtOAc
  4. washThe organic solution was washed with aqueous NaCl
  5. dry with materialdried over Na2SO4
  6. customEvaporation of the EtOAc
  7. customgave a residue that
  8. washeluting with an EtOAc/CH2Cl2 mixture

出典と根拠

ORDレコード
ord-44bb76e2c2ce4a188bb593dcddb238e2
出典データセット
uspto-grants-1984_12
特許番号
US04490384

反応ノート

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