Toluene → 3-Fluoro-4-phenylmethoxyaniline

HRID 445476노트

반응식

HRID 445476 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:10]=1[F:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.C([O-])=O.[NH4+]>[Fe].O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:10]=1[F:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 1140TolueneHCID 2723923Ammonium formateHCID 220309121-(Benzyloxy)-2-fluoro-4-nitrobenzene

생성물 1

HCID 219518923-Fluoro-4-phenylmethoxyaniline수율 87.2%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 962Water용매

실험 절차

A mixture of 1-benzyloxy-2-fluoro-4-nitro-benzene (44 g, 178 mmol), toluene (400 ml), ammonium formate (35 g), iron (30 g), and water (400 ml) was heated to reflux with stirring overnight. The reaction mixture was filtered through celite and washed with ethyl acetate (400 ml). The organic layer was separated and washed with brine (300 ml), dried over sodium sulfate and concentrated to give 4-benzyloxy-3-fluoro-phenylamine as an oil (33.7 g, 87%). 1H NMR (400 MHz, CDCl3): δ 7.41-7.29 (m, 5H), 6.79 (t, 1H), 6.45 (dd, 1H), 6.14 (dd, 1H), 5.02 (s, 2H), 3.50 (s, 2H). LC/MS: (M+1) 218.

후처리

  1. temperaturewas heated
  2. temperatureto reflux
  3. filtrationThe reaction mixture was filtered through celite
  4. washwashed with ethyl acetate (400 ml)
  5. customThe organic layer was separated
  6. washwashed with brine (300 ml)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d759809edca445149461e1d4267441ae
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476298B2

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