Sodium Hydroxide → Tert-butyl 4-(trifluoromethoxy)phenylcarbamate

HRID 1270788Notes

Reaction equation

HRID 1270788 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1.[C:13](=O)([O:19]C(C)(C)C)[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].[OH-].[Na+]>C1COCC1>[C:13]([NH:8][C:7]1[CH:9]=[CH:10][C:4]([O:3][C:2]([F:11])([F:12])[F:1])=[CH:5][CH:6]=1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:19]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 6008484-(Trifluoromethoxy)anilineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 11196668Tert-butyl 4-(trifluoromethoxy)phenylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Trifluoromethoxyaniline (100 g, 0.58 mol), di-tert-butyl carbonate (127 g, 0.58 mol) and 1 N NaOH solution (250 mL) are dissolved in THF (200 mL) and stirred at room temperature for 12 hours. The reaction mixture is extracted with EtOAc (500 mL). The organic layer is washed with 1 N HCl (500 mL), brine (250 mL) and dried (MgSO4). The solvent is removed by rotary evaporator to give N-BOC-4-trifluoromethoxyaniline.

Workup

  1. extractionThe reaction mixture is extracted with EtOAc (500 mL)
  2. washThe organic layer is washed with 1 N HCl (500 mL), brine (250 mL)
  3. dry with materialdried (MgSO4)
  4. customThe solvent is removed by rotary evaporator

Sources & evidence

ORD record
ord-5b342cadb8244c19a82371722e2f902c
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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