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

HRID 1846502ノート

反応式

HRID 1846502 の反応式
[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

参加物

6

反応物 4

HCID 7498Benzyl Bromide2 回HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 669782964-Amino-3-methyl-5-nitrophenol

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2bbad882c8064187bd54b92a49f4c1ac
出典データセット
uspto-grants-2015_02
特許番号
US08952014B2

反応ノート

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