Hydrochloric Acid → HCID 66606141, compound

HRID 1811053Notes

Reaction equation

HRID 1811053 reaction equation
[Br:1][C:2]1[C:3]([F:11])=[C:4]([NH:8][CH:9]=O)[CH:5]=[CH:6][CH:7]=1.CSC.B.Cl>C1COCC1>[Br:1][C:2]1[C:3]([F:11])=[C:4]([CH:5]=[CH:6][CH:7]=1)[NH:8][CH3:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12423031(Dimethyl sulfide)trihydroboronHCID 86642944HCID 86642944, compound

Product 1

HCID 66606141HCID 66606141, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Step 2 A suspension of N-(3-bromo-2-fluorophenyl)formamide (216 mg, 0.991 mmol) in THF (8 mL) was treated with borane dimethyl sulfide complex (2.0 M in THF, 1.486 mL, 2.97 mmol) and the resulting mixture was heated at reflux for 2 h. 1 M hydrochloric acid was added and the mixture was again heated at reflux for 1 h. The mixture was cooled to rt and concentrated and the residue was partitioned between NaHCO3 (aq) and EtOAc. The organic phase was washed with brine, dried and concentrated to provide 3-bromo-2-fluoro-N-methylaniline as a light yellow oil (60 mg, 30%). Mass spectrum m/z 204, 206 (M+H)+.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 2 h
  3. temperaturethe mixture was again heated
  4. temperatureat reflux for 1 h
  5. concentrationconcentrated
  6. customthe residue was partitioned between NaHCO3 (aq) and EtOAc
  7. washThe organic phase was washed with brine
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-341cf64a8f0546eebecd29bea3a36a4b
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

Loading…