Sodium Hydroxide → 3-Fluoro-5-[(methylsulfonyl)methyl]aniline

HRID 514709ノート

反応式

HRID 514709 の反応式
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([CH2:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:3]=1.[OH-].[Na+]>Cl.C1COCC1.[Cl-].[Ti+3].[Cl-].[Cl-]>[F:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([CH2:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:3]=1)[NH2:8]

参加物

6

反応物 2

HCID 14798Sodium HydroxideHCID 70976499HCID 70976499、化合物

生成物 1

HCID 867296143-Fluoro-5-[(methylsulfonyl)methyl]aniline収率 30.1%

試薬・触媒・溶媒 3

HCID 10313229titanium(III) trichloride触媒HCID 313Hydrochloric Acid溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Titanium(III)chloride solution (about 15%) in about 10% hydrochloric acid (29 mL, Merck Schuchardt OHG) was added to a stirred solution of crude 1-fluoro-3-[(methylsulfonyl)methyl]-5-nitrobenzene (1.00 g) in THF (45 mL) at room temperature and the batch was stirred for 16 hours. The batch was cooled with an ice bath while 1N sodium hydroxide solution was added to raise the pH value of the reaction mixture to 8-9. It was stirred for 30 minutes at this temperature before the batch was extracted with ethyl acetate (2×). The combined organic phases were washed with brine, filtered using a Whatman filter and concentrated. The residue was purified by column chromatography (hexane/ethyl acetate 1:1 to ethyl acetate) to give the desired product (262 mg; 1.29 mmol).

後処理

  1. additionwas added
  2. temperatureto raise the pH value of the reaction mixture to 8-9
  3. stirringIt was stirred for 30 minutes at this temperature before the batch
  4. extractionwas extracted with ethyl acetate (2×)
  5. washThe combined organic phases were washed with brine
  6. filtrationfiltered
  7. filtrationfilter
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography (hexane/ethyl acetate 1:1 to ethyl acetate)

出典と根拠

ORDレコード
ord-596b7721ab6840bea4c3a49fcc47f217
出典データセット
uspto-grants-2015_08
特許番号
US09108926B2

反応ノート

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