Sodium → 1-(2-Fluoro-3-methoxy-6-nitrophenyl)propan-2-one

HRID 454220ノート

反応式

HRID 454220 の反応式
[CH3:1][O-:2].[Na+].[Na].F[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]([CH2:15][C:16]([O:20]C)(OC)[CH3:17])[C:7]=1[F:22]>CO>[C:16]([CH2:15][C:8]1[C:7]([F:22])=[C:6]([O:2][CH3:1])[CH:11]=[CH:10][C:9]=1[N+:12]([O-:14])=[O:13])(=[O:20])[CH3:17]

参加物

5

反応物 3

HCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 22030751HCID 22030751、化合物

生成物 1

HCID 220307431-(2-Fluoro-3-methoxy-6-nitrophenyl)propan-2-one収率 90%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
5 °C

実験手順

A solution of sodium methoxide (freshly prepared from sodium (1.71 g) and methanol (35 ml)) was added to a solution of 1,2-difluoro-3-(2,2-dimethoxypropyl)-4-nitrobenzene (16.2 g, 62 mmol), (prepared as described above), in methanol (200 ml) cooled at 5° C. The mixture was left to warm to ambient temperature and was stirred for 3 days. The volatiles were removed under vacuum and the residue was partitioned between ethyl acetate and 2N hydrochloric acid (1 ml). The organic layer was concentrated to a total volume of 100 ml and THF (100 ml) and 6N hydrochloric acid (25 ml) were added. The mixture was stirred for 1 hour at ambient temperature. The volatiles were removed under vacuum and the residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with water, brine, dried (MgSO4) and evaporated. The residue was purified by column chromatography eluting with ethyl acetate/petroleum ether (3/7) to give 3-acetylmethyl-2-fluoro-1-methoxy-4-nitrobenzene (12.7 g, 90%).

後処理

  1. waitThe mixture was left
  2. temperatureto warm to ambient temperature
  3. customThe volatiles were removed under vacuum
  4. customthe residue was partitioned between ethyl acetate and 2N hydrochloric acid (1 ml)
  5. concentrationThe organic layer was concentrated to a total volume of 100 ml and THF (100 ml) and 6N hydrochloric acid (25 ml)
  6. additionwere added
  7. stirringThe mixture was stirred for 1 hour at ambient temperature
  8. customThe volatiles were removed under vacuum
  9. customthe residue was partitioned between ethyl acetate and water
  10. customThe organic layer was separated
  11. washwashed with water, brine
  12. dry with materialdried (MgSO4)
  13. customevaporated
  14. customThe residue was purified by column chromatography
  15. washeluting with ethyl acetate/petroleum ether (3/7)

出典と根拠

ORDレコード
ord-9442689db3e0417b98736ee3f4ee3471
出典データセット
uspto-grants-2013_07
特許番号
US08492560B2

反応ノート

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