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

HRID 32794

Reaction equation

HRID 32794 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

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%).

Workup

  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))

Sources & evidence

ORD record
ord-fa511c497d154a0b80b25451fc45b008
Source dataset
uspto-grants-2008_09
Patent number
US07427630B2

Linked notes

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