(2-Amino-3-trifluoromethyl-phenyl)-methanol → HCID 86701174, compound

HRID 572133Notes

Reaction equation

HRID 572133 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:12][OH:13]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[NH2:1][C:2]1[C:7]([C:8]([F:9])([F:10])[F:11])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:12]=[O:13]

Participants

4

Reactant 1

HCID 20319007(2-Amino-3-trifluoromethyl-phenyl)-methanol

Product 1

HCID 86701174HCID 86701174, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

Manganese dioxide (27 g, 0.32 mol) was added to a solution of [2-amino-3-(trifluoromethyl)phenyl]methanol (12.0 g, 0.063 mol) in DCM (150 mL) and the mixture was stirred for 18 h at room temperature. After this time, more manganese dioxide (27 g, 0.32 mol) was added, and the reaction mixture was left for a further 18 h. The reaction mixture was filtered through Celite, then the solvent was removed in vacuo to afford the title compound (9.5 g, 80%) as an orange oil. δH (DMSO-d6) 9.93 (s, 1H), 7.68 (m, 2H), 6.82 (m, 3H).

Workup

  1. waitthe reaction mixture was left for a further 18 h
  2. filtrationThe reaction mixture was filtered through Celite
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-71b147b0ceea463597170e7581ebf1be
Source dataset
uspto-grants-2015_05
Patent number
US09029392B2

Reaction notes

Loading…