Hydrochloric Acid → 3-(Difluoromethoxy)-2-fluoroaniline

HRID 1527450Notes

Reaction equation

HRID 1527450 reaction equation
[F:1][CH:2]([F:14])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-])=O)[C:5]=1[F:13].[Sn](Cl)Cl.Cl.[OH-].[Na+]>CC(O)C.O>[F:14][CH:2]([F:1])[O:3][C:4]1[C:5]([F:13])=[C:6]([NH2:10])[CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 463115911-(Difluoromethoxy)-2-fluoro-3-nitrobenzene

Product 1

HCID 682835143-(Difluoromethoxy)-2-fluoroaniline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of 1-difluoromethoxy-2-fluoro-3-nitro-benzene (2.16 g, 10.43 mmol) and tin(II) chloride (6.92 g, 36.5 mmol) in 2-propanol (100 ml) was added carefully HCl (37%, 10.28 ml, 125 mmol) and the mixture was stirred for 30 min at 110° C. The reaction mixture was cooled to RT, diluted with water and the pH adjusted to 10 by addition of 2N NaOH. The mixture was extracted with EtOAc and the organic layer was dried over Na2SO4, filtered and concentrated to afford the titled compound. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 7.06 (t, 1H), 6.95 (m, 1H), 6.87 (m, 1H), 6.55 (td, 1H), 5.04 (bs, 2H). tR (HPLC conditions f): 1.93 min.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. extractionThe mixture was extracted with EtOAc
  3. dry with materialthe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2ebff932bb374ca88306b7364208feff
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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