Triethylamine → tert-Butyl (4-bromo-2-methylphenyl)carbamate

HRID 32794

반응식

HRID 32794 반응식
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH3:9])[CH:3]=1.CCN(CC)CC.[O:17](C(OC(C)(C)C)=O)[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=O.[NH4+].[Cl-]>O1CCOCC1.O.CCOC(C)=O>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:18](=[O:17])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[C:4]([CH3:9])[CH:3]=1

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 114234-Bromo-2-methylanilineHCID 25517Ammonium ChlorideHCID 90495Di-tert-butyl dicarbonate

생성물 1

HCID 2735638tert-Butyl (4-bromo-2-methylphenyl)carbamate수율 79.4%

시약·촉매·용매 3

HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

To a solution of 4-bromo-2-methylaniline (1 g, 5.37 mmol,) in 1,4-dioxane (11 mL) and H2O (4 mL), at r.t., were added Et3N (2.7 mL, 1.2 eq) and BOC2O (4.2 g, 1.2 eq). The reaction mixture was stirred at r.t. for 96 hr. Sat.aq. NH4Cl and EtOAc (20 mL) were added and the phases were separated. The aqueous layer was further extracted with EtOAc (2×20 mL). The combined organic extracts were dried over anh. Na2SO4, the solids were filtered and the solvent evaporated. The residue was purified on an SCX cartridge (CH2Cl2, MeOH and NH3(0.5 M in MeOH)) to give the title compound as a white solid (1.22 g, 79%).

후처리

  1. customthe phases were separated
  2. extractionThe aqueous layer was further extracted with EtOAc (2×20 mL)
  3. dry with materialThe combined organic extracts were dried over anh. Na2SO4
  4. filtrationthe solids were filtered
  5. customthe solvent evaporated
  6. customThe residue was purified on an SCX cartridge (CH2Cl2, MeOH and NH3(0.5 M in MeOH))

출처 및 근거

ORD 기록
ord-fa511c497d154a0b80b25451fc45b008
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07427630B2

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