1,1-Dimethylethyl N-(2-fluoro-6-methylphenyl)carbamate → 2-Fluoro-6-methylaniline

HRID 1372529Notes

Reaction equation

HRID 1372529 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9]C(=O)OC(C)(C)C>FC(F)(F)C(O)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH2:9]

Participants

3

Reactant 1

HCID 587796871,1-Dimethylethyl N-(2-fluoro-6-methylphenyl)carbamate

Product 1

HCID 141554112-Fluoro-6-methylaniline

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The crude carbamate from step 2 (7.2 g, 32 mmol) was treated with trifluoroacetic acid (30 mL). The resulting solution was stirred at room temperature for 30 minutes, then most of trifluoroacetic acid was evaporated under vacuum. The residue was diluted with CH2Cl2 and poured into a slurry of solid Na2CO3 in CH2Cl2. The resulting slurry was carefully treated with EtOAc to increase product solubility, then filtered through a pad of silica gel and the product washed off with EtOAc. The filtrate and washings were concentrated under vacuum to afford 2-fluoro-6-methylaniline as a yellow solid.

Workup

  1. custommost of trifluoroacetic acid was evaporated under vacuum
  2. additionThe residue was diluted with CH2Cl2
  3. additionpoured into a slurry of solid Na2CO3 in CH2Cl2
  4. additionThe resulting slurry was carefully treated with EtOAc
  5. temperatureto increase product solubility
  6. filtrationfiltered through a pad of silica gel
  7. washthe product washed off with EtOAc
  8. concentrationThe filtrate and washings were concentrated under vacuum

Sources & evidence

ORD record
ord-2573bcb19f3a4200b0e197f5cc2d89bc
Source dataset
uspto-grants-2007_01
Patent number
US07157604B2

Reaction notes

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