Hydrochloric Acid → 5-Bromo-3-(dichloromethyl)-2-nitrothiophene

HRID 1799536

반응식

HRID 1799536 반응식
[Br:1][C:2]1[S:3][C:4]([N+:7]([O-:9])=[O:8])=[CH:5][CH:6]=1.[CH:10](Cl)([Cl:12])[Cl:11].CC(C)([O-])C.[K+].Cl>CN(C=O)C.C1COCC1>[Br:1][C:2]1[S:3][C:4]([N+:7]([O-:9])=[O:8])=[C:5]([CH:10]([Cl:12])[Cl:11])[CH:6]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 832222-Bromo-5-nitrothiopheneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 595256075-Bromo-3-(dichloromethyl)-2-nitrothiophene

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

A solution of 2-bromo-5-nitrothiophene (29 g, 139 mmol) and chloroform (12.37 mL, 153 mmol) in DMF (110 mL) was added dropwise to a solution of potassium tert-butoxide (62.6 g, 558 mmol) in THF (225 mL)/DMF (180 mL). The internal temperature was monitored and maintained at <−60° C. during the addition. Upon complete addition, the reaction was stirred at −78° C. for 30 minutes. 2 N HCl was added and the products were extracted into EtOAc (3×). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Purification of the residue by flash silica gel column chromatography (0-10% EtOAc-hexanes) gave the title compound as a brown oil.

후처리

  1. temperaturemaintained at <−60° C. during the addition
  2. additionUpon complete addition
  3. extractionthe products were extracted into EtOAc (3×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by flash silica gel column chromatography (0-10% EtOAc-hexanes)

출처 및 근거

ORD 기록
ord-a8a855276a1c49779e44bcde91388d6e
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08344144B2

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