Pyridine → 4-Bromo-2,6-difluorophenethyl acetate

HRID 1525905ノート

反応式

HRID 1525905 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([CH2:9][CH2:10][OH:11])=[C:4]([F:12])[CH:3]=1.N1C=CC=CC=1.[C:19](OC(=O)C)(=[O:21])[CH3:20]>ClCCl.CN(C)C1C=CN=CC=1>[C:19]([O:11][CH2:10][CH2:9][C:5]1[C:4]([F:12])=[CH:3][C:2]([Br:1])=[CH:7][C:6]=1[F:8])(=[O:21])[CH3:20]

参加物

6

反応物 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 672934294-Bromo-2,6-difluorobenzeneethanol

生成物 1

HCID 712708734-Bromo-2,6-difluorophenethyl acetate収率 84.9%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

A solution of 2-(4-bromo-2,6-difluorophenyl)ethanol (1.392 mmol) in dichloromethane (2 mL) was treated with pyridine (4.00 mL), acetic anhydride (4.18 mmol), and 4-(dimethylamino)pyridine (0.070 mmol). The reaction was stirred at room temperature for three days. At this point, the reaction contents were concentrated to in vacuo to minimum volume. The material was diluted with water (50 mL) and was extracted twice with ethyl acetate. The combined organic layers were washed with saturated aq sodium bicarbonate, twice with brine, dried over sodium sulfate, filtered and concentrated in vacuo to afford the title compound as a beige oil (330 mg, 76% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.95 (s, 3 H) 2.91 (t, J=6.32 Hz, 2 H) 4.18 (t, J=6.44 Hz, 2 H) 7.47 (d, J=7.07 Hz, 2 H).

後処理

  1. customAt this point, the reaction contents
  2. concentrationwere concentrated to in vacuo to minimum volume
  3. additionThe material was diluted with water (50 mL)
  4. extractionwas extracted twice with ethyl acetate
  5. washThe combined organic layers were washed with saturated aq sodium bicarbonate, twice with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-a0718a7094f84735b5936dcc8acf17aa
出典データセット
uspto-grants-2015_07
特許番号
US09084794B2

反応ノート

読み込み中…