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

HRID 1525905노트

반응식

HRID 1525905 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 712708734-Bromo-2,6-difluorophenethyl acetate수율 84.9%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a0718a7094f84735b5936dcc8acf17aa
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09084794B2

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