Diethyl Ether → Dimethyl-thiocarbamic acid S-(4-bromo-2-hydroxymethyl-6-nitro-phenyl)ester

HRID 1747486노트

반응식

HRID 1747486 반응식
C([O:3][C:4](=O)[C:5]1[CH:10]=[C:9]([Br:11])[CH:8]=[C:7]([N+:12]([O-:14])=[O:13])[C:6]=1[S:15][C:16](=[O:20])[N:17]([CH3:19])[CH3:18])C.C(OCC)C.B>C1COCC1>[Br:11][C:9]1[CH:8]=[C:7]([N+:12]([O-:14])=[O:13])[C:6]([S:15][C:16](=[O:20])[N:17]([CH3:19])[CH3:18])=[C:5]([CH2:4][OH:3])[CH:10]=1

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 6331Borane2회HCID 594976075-Bromo-2-dimethylcarbamoylsulfanyl-3-nitro-benzoic acid ethyl ester

생성물 1

HCID 59497682Dimethyl-thiocarbamic acid S-(4-bromo-2-hydroxymethyl-6-nitro-phenyl)ester수율 91%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

5-Bromo-2-dimethylcarbamoylsulfanyl-3-nitro-benzoic acid ethyl ester (3.0 g, 9.4 mmol) is taken up in THF (40 mL)/diethyl ether (10 mL) and cooled to zero with an ice bath. Borane in THF (1M, 20 mL, 2.1 mmol) is added dropwise to the reaction and then the reaction warmed to room temperature. An additional equivalent of borane is added, and the reaction warmed to 45° C. The reaction is stirred at 45° C. for 4 hours and then the reaction cooled to zero and quenched by the slow addition of saturated NH4Cl. The reaction is poured into water and then extracted with ethyl acetate. The combined organic layers were dried filtered and evaporated. The residue is purified on silica gel with DCM/MeOH as the eluent to afford 2.5 g (91%) of the title product. LCMS (ESMS): m/z 336.9 (M+H+).

후처리

  1. temperaturecooled to zero with an ice bath
  2. temperaturethe reaction warmed to 45° C
  3. temperaturethe reaction cooled to zero
  4. customquenched by the slow addition of saturated NH4Cl
  5. additionThe reaction is poured into water
  6. extractionextracted with ethyl acetate
  7. customThe combined organic layers were dried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue is purified on silica gel with DCM/MeOH as the eluent

출처 및 근거

ORD 기록
ord-5bbd51f808c34fc3986367ee0ea77503
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150556B2

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