1-Chloro-4-fluoro-2-nitrobenzene → 2-Amino-4-fluorobenzene-1-thiol

HRID 407282

反応式

HRID 407282 の反応式
Cl[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[N+:9]([O-])=O.O.O.O.O.O.O.O.O.O.[S-2:21].[Na+].[Na+]>O>[NH2:9][C:3]1[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=1[SH:21]

参加物

4

反応物 2

HCID 676591-Chloro-4-fluoro-2-nitrobenzeneHCID 73972Sodium sulfide nonahydrate

生成物 1

HCID 111054802-Amino-4-fluorobenzene-1-thiol収率 25%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a solution of 2-chloro-5-fluoronitrobenzene (1.81 g, 10.31 mmol) dissolved in 30 mL of deionized water at room temperature was added sodium sulfide nonahydrate (9.90 g, 41.24 mmol) in a single portion. The resulting solution was heated to reflux and stirred under nitrogen for 32 hours. The resulting light yellow solution was then cooled to room temperature and was washed with 5×50 mL of ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate, filtered, and evaporated to yield a yellow oil. The crude material was purified by flash chromatography eluting with CH2Cl2:MeOH=10:1 to yield 0.36 g (25%) of the title compound. MS (m/z, ES+): 144.0 (M+1, 100%); IR (KBr): 3430, 3340, 1615, 1573, 1482, 1281, 1248, 1172, 1124, 1044, 975, 840, 792 cm−1; 1H NMR (300 MHz, ppm, DMSO-d6) δ: 6.89 (dt, 1H), 6.50 (dd, 1H), 6.21 (dt, 1H), 5.80 (br s, 2H).

後処理

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux
  3. washwas washed with 5×50 mL of ethyl acetate
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto yield a yellow oil
  8. customThe crude material was purified by flash chromatography
  9. washeluting with CH2Cl2

出典と根拠

ORDレコード
ord-022647257f5a424ca792ce8d58f398c5
出典データセット
uspto-grants-2014_06
特許番号
US08754233B2

関連ノート

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