Tert-butyl 2-methyl-4-(trifluoromethyl)phenylcarbamate → 4-Amino-3-methylbenzotrifluoride

HRID 913806Notes

Reaction equation

HRID 913806 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[NH:12]C(=O)OC(C)(C)C>FC(F)(F)C(O)=O>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:5]=[CH:4][C:3]=1[NH2:12]

Participants

3

Reactant 1

HCID 53420019Tert-butyl 2-methyl-4-(trifluoromethyl)phenylcarbamate

Product 1

HCID 137504374-Amino-3-methylbenzotrifluoride

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 2-methyl-4-(trifluoromethyl)phenylcarbamate (1 1.6 g, 42 mmol) was dissolved in trifluoroacetic acid (17% in dichloromethane, 90 mL) and stirred at room temperature for 30 min. The reaction was concentrated and taken up in water/pentane. The aqueous was neutralized with saturated sodium bicarbonate, and the layers separated. The organics were dried over magnesium sulfate and concentrated to give 7.8 g (quant.). 1H-NMR (CDCl3, 500 MHz) δ 7.25-7.40 (m, 2H), 6.67 (d, J=7.9 Hz, 1H), 3.87 (bs, 2H), 2.18 (s, 3H); 13C-NMR (CDCl3, 126 MHz) δ 147.7, 127.5 (q, J=3.8 Hz), 125.0 (q, J=271 Hz), 124.4 (q, J=3.8 Hz), 120.3 (q, J=33 Hz), 114.1, 17.2. Mass spec.: 176.03 (MH)+.

Workup

  1. concentrationThe reaction was concentrated
  2. customthe layers separated
  3. dry with materialThe organics were dried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give 7.8 g (quant.)

Sources & evidence

ORD record
ord-4ee1f89280194c9391a06ea38c166140
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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