(2-Amino-6-fluorophenyl)methanol → 2-Amino-6-fluorobenzaldehyde

HRID 448919Notes

Reaction equation

HRID 448919 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][OH:10]>ClCCl.O=[Mn]=O>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH:9]=[O:10]

Participants

4

Reactant 1

HCID 11521092(2-Amino-6-fluorophenyl)methanol

Product 1

HCID 217194752-Amino-6-fluorobenzaldehydeYield 51.1%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To (2-amino-6-fluoro-phenyl)-methanol (2.49 g, 17.3 mmol) in dichloromethane (30 mL) was added MnO2 (3.01 g, 34.7 mmol, activated). The mixture was refluxed for 3 hrs and then filtered over celite. The mixture was concentrated and purified via silica gel flash chromatography (eluting with 30% ethyl acetate in hexane) to give 2-amino-6-fluoro-benzaldehyde as a yellow solid (1.23 g). tR=2.20 min. (method 1)

Workup

  1. temperatureThe mixture was refluxed for 3 hrs
  2. filtrationfiltered over celite
  3. concentrationThe mixture was concentrated
  4. custompurified via silica gel flash chromatography (eluting with 30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-4f5244801e9e415daa645eb9ccac5c3b
Source dataset
uspto-grants-2013_07
Patent number
US08481738B2

Reaction notes

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