Bromine → 2-(Benzyloxy)-4-bromo-6-fluoroaniline

HRID 889241ノート

反応式

HRID 889241 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[C:10]=1[NH2:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:17]Br>CO.CC(O)=O>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([Br:17])[CH:12]=[C:11]([F:15])[C:10]=1[NH2:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 24408BromineHCID 15219197HCID 15219197、化合物

生成物 1

HCID 684315652-(Benzyloxy)-4-bromo-6-fluoroaniline

試薬・触媒・溶媒 1

HCID 10129899Acetic acid methanol溶媒2 回

実験手順

To a solution of 2-benzyloxy-6-fluorophenylamine (7.29 g, 33.6 mmol) in MeOH/HOAc (3:1 v/v, 30 mL) at 0° C. is added bromine (2.2 mL, 47 mmol) in MeOH/HOAc (3:1 v/v, 4 mL) drop wise. After it is stirred for 4 h, the reaction is completed by LC/MS. The reaction mixture is concentrated, and the residue is stirred with EtOAc and 1N NaOH to dissolve solid. Additional base is added to make the aqueous alkaline, and then EtOAc layer is separated. The organic phase is washed with brine, dried and filtered. The concentrated residue is purified to give the title compound: 1H NMR (CDCl3) 7.39 (m, 5H), 6.86 (dd, 1H, J=9.8, 2.0 Hz), 6.81 (m, 1H), 5.05 (s, 2H), 3.77 (br s, 2H); MS (M+H)+=296, 298.

後処理

  1. concentrationThe reaction mixture is concentrated
  2. stirringthe residue is stirred with EtOAc and 1N NaOH
  3. dissolutionto dissolve solid
  4. additionAdditional base is added
  5. customEtOAc layer is separated
  6. washThe organic phase is washed with brine
  7. customdried
  8. filtrationfiltered
  9. customThe concentrated residue is purified

出典と根拠

ORDレコード
ord-40de82d4583a4eb6abad515e88615384
出典データセット
uspto-grants-2012_08
特許番号
US08252820B2

反応ノート

読み込み中…