2-Fluoro-4-nitroanisole → 1-Fluoro-4-(isocyanomethyl)-2-methoxy-5-nitrobenzene

HRID 921016

반응식

HRID 921016 반응식
[CH3:1]C(C)([O-])C.[K+].[F:7][C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:9]=1[O:17][CH3:18].ClC1C=CC(OC[C:26]#[N:27])=CC=1>CN(C=O)C>[F:7][C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[C:11]([CH2:1][N+:27]#[C-:26])=[CH:10][C:9]=1[O:17][CH3:18]

참가 물질

5

반응물 3

HCID 2231042-Fluoro-4-nitroanisoleHCID 3064442-(4-Chlorophenoxy)acetonitrileHCID 23665647Potassium tert-butoxide

생성물 1

HCID 867126191-Fluoro-4-(isocyanomethyl)-2-methoxy-5-nitrobenzene수율 24.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

Potassium t-butoxide (15.74 g, 140 mmol) in DMF (50 mL) was added to a solution of 2-fluoro-1-methoxy-4-nitrobenzene (12 g, 70.1 mmol) and 2-(4-chlorophenoxyl)acetonitrile (11.75 g, 70.1 mmol) in DMF (100 mL) at −20° C. The reaction mixture was stirred for 1 h and then quenched with water. The aqueous layer was extracted with ethyl acetate. Organic layer was separated, washed with brine, dried over sodium sulphate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography using 3% ethyl acetate in hexane to afford title compound (3.6 g, 23.21%) as a solid. 1H NMR (400 MHz, CDCl3): δ 8.05 (d, J=10.84 Hz, 1H), 7.27-7.23 (m, 1H), 4.28 (s, 2H), 4.05 (s, 3H); ESI-MS m/z=209 (M−H)−; LCMS Purity: 95%

후처리

  1. customquenched with water
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. customOrganic layer was separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography

출처 및 근거

ORD 기록
ord-3bc4c05f356c41458847ae49013ab8ac
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273069B2

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