Toluene → 3-Fluoro-4-phenylmethoxyaniline

HRID 445473노트

반응식

HRID 445473 반응식
C([O-])=O.[NH4+].[CH2:5]([O:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][C:14]=1[F:22])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C1(C)C=CC=CC=1>[Fe].O>[CH2:5]([O:12][C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][C:14]=1[F:22])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

참가 물질

6

반응물 3

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

생성물 1

HCID 219518923-Fluoro-4-phenylmethoxyaniline수율 101.3%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 962Water용매

실험 절차

A mixture of iron powder (45.2 g, 0.809 g atoms), ammonium formate (53.6 g, 0.850 mol), 1-benzyloxy-2-fluoro-4-nitrobenzene (50.0 g, 0.200 mol), toluene (400 mL) and water (400 mL) was heated to reflux overnight. The mixture was filtered through Celite and washed with hot ethyl acetate. The combined organic layers were washed with water and brine, then dried over sodium sulfate and concentrated to afford 4-benzyloxy-3-fluoroaniline (44 g, 100%). 1H NMR (400 MHz, d6-DMSO): δ 7.43-7.26 (m, 5H), 6.90 (dd, 1H), 6.49 (dd, 1H), 6.34 (m, 1H), 4.99 (br s, 2H), 4.98 (s, 2H); 13C NMR (100 MHz, d6-DMSO): δ 171.1, 155.1, 152.7, 144.9, 138.0, 137.2, 129.6, 129.0, 128.5, 118.9, 110.0, 102.9, 72.5; IR (cm−1): 1510, 1454, 1277, 1215, 1126, 1007, 957, 843, 800, 789, 739, 694, 604; LC/MS (M+H=218).

후처리

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. filtrationThe mixture was filtered through Celite
  4. washwashed with hot ethyl acetate
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3a57777330924072b53206d7e73b45bd
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476298B2

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