Ammonium Chloride → HCID 86713632, 화합물

HRID 1430475노트

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HRID 1430475 반응식
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-])=O)=[CH:4][C:3]=1[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].[Cl-].[NH4+]>CCO.[Fe]>[NH2:9][C:5]1[C:6]([F:8])=[CH:7][C:2]([Br:1])=[C:3]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:4]=1

참가 물질

5

반응물 2

HCID 25517Ammonium ChlorideHCID 68984776HCID 68984776, 화합물

생성물 1

HCID 86713632HCID 86713632, 화합물수율 93.4%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

반응 조건

온도
55 °C

실험 절차

A solution of ethyl 2-(2-bromo-4-fluoro-5-nitrophenyl)acetate (2.127 g, 6.95 mmol) in EtOH (70 mL) was treated with iron powder (3.88 g, 69.5 mmol) and satd ammonium chloride (14.48 mL, 69.5 mmol) and heated to 55° C. for 1 h. The mixture was cooled to RT, filtered through a pad of diatomaceous earth, rinsed well with EtOH and the organics concentrated under reduced pressure. The resulting aqueous residue was treated with satd. NaHCO3, extracted with EtOAc (2×) and the combined organics were washed with water, dried (MgSO4), and concentrated to afford ethyl 2-(5-amino-2-bromo-4-fluorophenyl)acetate (1.792 g, 93% yield) as an amber oil. 1H NMR (400 MHz, DMSO-d6): δ 7.25 (d, 1H), 6.76 (d, 1H), 5.35 (s, 2H), 4.08 (q, 2H), 3.61 (s, 2H), 1.18 (t, 3H); MS (ESI) m/z: 278.0 [M+H]+.

후처리

  1. temperatureThe mixture was cooled to RT
  2. filtrationfiltered through a pad of diatomaceous earth
  3. washrinsed well with EtOH
  4. concentrationthe organics concentrated under reduced pressure
  5. additionThe resulting aqueous residue was treated with satd
  6. extractionNaHCO3, extracted with EtOAc (2×)
  7. washthe combined organics were washed with water
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4b20a07ab6e54e9b882100b99123776a
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940756B2

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