Ammonium Chloride → HCID 86713632、化合物

HRID 1430475ノート

反応式

HRID 1430475 の反応式
[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

参加物

5

反応物 2

HCID 25517Ammonium ChlorideHCID 68984776HCID 68984776、化合物

生成物 1

HCID 86713632HCID 86713632、化合物収率 93.4%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 702Ethanol溶媒

反応条件

温度
55 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-4b20a07ab6e54e9b882100b99123776a
出典データセット
uspto-grants-2015_01
特許番号
US08940756B2

反応ノート

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