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

HRID 576583

反応式

HRID 576583 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

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-chlorophenoxy)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%

後処理

  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

出典と根拠

ORDレコード
ord-86656cf8dfcf4b7886ed57f417020fc1
出典データセット
uspto-grants-2015_05
特許番号
US09040517B2

関連ノート

読み込み中…