Tetrahydrofuran → 4-(3-Bromo-benzenesulfinyl)-5-nitro-thiophene-2-carbonitrile

HRID 132076노트

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HRID 132076 반응식
Br[C:2]1[CH:3]=[C:4]([C:10]#[N:11])[S:5][C:6]=1[N+:7]([O-:9])=[O:8].[Br:12][C:13]1[CH:14]=[C:15]([SH:19])[CH:16]=[CH:17][CH:18]=1.C(N(CC)CC)C.C1C[O:30]CC1>>[Br:12][C:13]1[CH:14]=[C:15]([S:19]([C:2]2[CH:3]=[C:4]([C:10]#[N:11])[S:5][C:6]=2[N+:7]([O-:9])=[O:8])=[O:30])[CH:16]=[CH:17][CH:18]=1

참가 물질

5

반응물 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 80597m-BromobenzenethiolHCID 218213104-Bromo-5-nitrothiophene-2-carbonitrile

생성물 1

HCID 668532114-(3-Bromo-benzenesulfinyl)-5-nitro-thiophene-2-carbonitrile수율 60%

실험 절차

A 12-L, three neck, round bottom flask equipped with a mechanical stirrer and temperature probe was charged with 4-Bromo-5-nitro-thiophene-2-carbonitrile (Example 25: step d; 273 g, 1.174 mol), 3-bromothiophenol (127 mL, 1.232 mol) and THF (4L). A cold water bath was added. Triethylamine (172 mL, 1.232 mol) was charged to a 250 mL addition funnel and added dropwise to the mixture over 45 min, resulting in a temperature increase from 16.9° C. to 22.3° C. After 1 hour, the reaction was complete and transferred in portions to a 5-L rotary evaporator bulb and concentrated to dryness under vacuum. The solids were transferred to a 10-L glass carboy, diluted with EtOAc (2L) and satd. NaHCO3 (2L) and stirred vigorously. The resulting solid precipitate was removed by filtration, washed with H2O (1L) and dried in a vacuum oven resulting in the title compound as a bright yellow powder (241.56 g, 60%). 1H-NMR (DMSO): δ 8.0 (1H, s), 7.8 (1H, d), 7.6 (1H, d), 7.3 (1H, t), 7.1 (1H, s).

후처리

  1. additionA cold water bath was added
  2. additionadded dropwise to the mixture over 45 min
  3. customresulting in a temperature
  4. temperatureincrease from 16.9° C. to 22.3° C
  5. concentrationconcentrated to dryness under vacuum
  6. additiondiluted with EtOAc (2L)
  7. customThe resulting solid precipitate was removed by filtration
  8. washwashed with H2O (1L)
  9. customdried in a vacuum oven

출처 및 근거

ORD 기록
ord-54563881c09d44c4bcad83b9fe88d375
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07385066B2

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