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

HRID 407282

반응식

HRID 407282 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

HCID 111054802-Amino-4-fluorobenzene-1-thiol수율 25%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-022647257f5a424ca792ce8d58f398c5
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754233B2

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