Benzyl Bromide → 4-(Benzyloxy)-2-methyl-6-nitroaniline

HRID 1846502노트

반응식

HRID 1846502 반응식
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([OH:11])=[CH:4][C:3]=1[CH3:12].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[OH-].[Na+]>CN(C=O)C>[CH2:19]([O:11][C:5]1[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]([NH2:1])=[C:3]([CH3:12])[CH:4]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

6

반응물 4

HCID 7498Benzyl Bromide2회HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 669782964-Amino-3-methyl-5-nitrophenol

생성물 1

HCID 669780234-(Benzyloxy)-2-methyl-6-nitroaniline

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

0.84 g (5.00 mmol) 4-amino-3-methyl-5-nitrophenol was placed in 10 mL DMF, combined with 0.78 g (5.50 mmol) potassium carbonate and stirred for 10 min at RT. Then 0.65 mL (5.50 mmol) benzylbromide were added and the mixture was stirred for a further 30 min at RT and for 1 h at 60° C. Another 0.33 mL benzylbromide were added and the mixture was stirred for 1 h at 60° C. The reaction mixture was poured onto ice water, extracted with ethyl acetate and evaporated down i.vac. The residue was purified by chromatography. The fractions containing product were combined and evaporated down i.vac. to leave the aqueous residue. This was neutralised with a 1M aqueous NaOH solution and extracted with ethyl acetate. The organic phase was evaporated down i.vac.

후처리

  1. stirringthe mixture was stirred for a further 30 min at RT and for 1 h at 60° C
  2. stirringthe mixture was stirred for 1 h at 60° C
  3. additionThe reaction mixture was poured onto ice water
  4. extractionextracted with ethyl acetate
  5. customevaporated down i.vac
  6. customThe residue was purified by chromatography
  7. additionThe fractions containing product
  8. customevaporated down i.vac
  9. customto leave the aqueous residue
  10. extractionextracted with ethyl acetate
  11. customThe organic phase was evaporated down i.vac

출처 및 근거

ORD 기록
ord-2bbad882c8064187bd54b92a49f4c1ac
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952014B2

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