2-(Trifluoromethyl)phenyl isocyanate → tert-Butyl (2-(trifluoromethyl)phenyl)carbamate

HRID 1435919Notes

Reaction equation

HRID 1435919 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]([F:13])([F:12])[F:11])=[C:2]=[O:3].[CH3:14][C:15]([CH3:18])([O-:17])[CH3:16].[K+]>C1COCC1>[F:11][C:10]([F:12])([F:13])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[NH:1][C:2](=[O:3])[O:17][C:15]([CH3:18])([CH3:16])[CH3:14]

Participants

4

Reactant 2

HCID 167942-(Trifluoromethyl)phenyl isocyanateHCID 23665647Potassium tert-butoxide

Product 1

HCID 15033883tert-Butyl (2-(trifluoromethyl)phenyl)carbamateYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-isocyanato-2-(trifluoromethyl)benzene (4.0 g, 21.4 mmol) in 50 mL of THF at 0° C. was added potassium tert-butoxide (32.0 mL of a 1M solution in THF, 32 mmol) dropwise. The reaction was allowed to stir for 3 h with warming to ambient temperature and then was quenched with 10 mL of water. The mixture was diluted with ethyl acetate and the organics were washed sequentially with 1N HCl, sat'd. aq. NaHCO3 and brine, dried (MgSO4) and concentrated. The residue was taken up in chloroform, filtered through a pad of silica gel and concentrated to afford 2.9 g (52%) of the title compound which was sufficiently pure to be used without further purification. 1H NMR (CDCl3): δ 8.13 (d, 1H, J=8.2 Hz), 7.56 (d, 1H, J=7.7 Hz), 7.52 (t, 1H, J=8.0 Hz), 7.14 (t, 1H, J=7.7 Hz), 6.80 (broad s, 1H), 1.53 (s, 9H).

Workup

  1. customwas quenched with 10 mL of water
  2. additionThe mixture was diluted with ethyl acetate
  3. washthe organics were washed sequentially with 1N HCl
  4. dry with materialaq. NaHCO3 and brine, dried (MgSO4)
  5. concentrationconcentrated
  6. filtrationfiltered through a pad of silica gel
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-33e2d8ed26024b4687ddf4f60985f5a7
Source dataset
uspto-grants-2009_11
Patent number
US07618980B2

Reaction notes

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