(2-(2-(Dimethylamino)ethylamino)-3-fluorophenyl)methanol → 2-(2-(Dimethylamino)ethylamino)-3-fluorobenzaldehyde
Reaction equation
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][NH:5][C:6]1[C:11]([F:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:13][OH:14]>C1(C)C=CC=CC=1.O=[Mn]=O>[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][NH:5][C:6]1[C:11]([F:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH:13]=[O:14]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
(2-(2-(dimethylamino)ethylamino)-3-fluorophenyl)methanol (536 mg, 2.525 mmol) and MnO2 (878.1 mg, 174.7 μL, 10.10 mmol) were heated to reflux in toluene (13 mL) overnight. The suspension was filtered through Celite with CH2Cl2 and concentrated on a rotary evaporator. The crude product was purified on 12 g Redisep ISCO column eluting with 4-55% EtOAc/Hexanes over 30 CV. 2-(2-(Dimethylamino)ethylamino)-3-fluorobenzaldehyde was identified by 1H-NMR and carried on to next reaction.