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

HRID 889241노트

반응식

HRID 889241 반응식
[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

참가 물질

4

반응물 2

HCID 24408BromineHCID 15219197HCID 15219197, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 10129899Acetic acid methanol용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-40de82d4583a4eb6abad515e88615384
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08252820B2

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