2-amino-4-benzylphenol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 2-fluoro-4-formylbenzoic acid (0.600 g, 3.57 mmol) in 15 mL DCM was added oxalyl dichloride (0.374 mL, 4.28 mmol) and N,N-dimethylformamide (0.00261 g, 0.0357 mmol) (a few drops). The mixture was allowed to stir for several h, treated with additional (COCl)2 (0.100 mL), stirred further for 1 h, concentrated in vacuo, and the semi-solid was suspended in 15 mL THF. N,N-diisopropylethylamine (0.808 mL, 4.64 mmol) was added followed by 2-amino-4-benzylphenol (0.711 g, 3.57 mmol). After 4 h, the reaction was treated with EtOAc, water, and 1N HCl. The organic layer was washed 1× brine, dried over sodium sulfate, filtered, and concentrated. The material was purified by silica gel chromatography to give title compound as a solid. MS (ESI) m/z: Calculated: 349.1; Observed: 347.7 (M−−1). stirred further for 1 h concentrated in vacuo The organic layer was washed 1× brine dried over sodium sulfate filtered concentrated The material was purified by silica gel chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 10% Palladium on carbon, Pearlman, (50% wet) (2.3 g, 2.2 mmol) and 4-benzyl-2-nitrophenol (5.00 g, 22 mmol) were combined under nitrogen and diluted with 80 mL MeOH delivered via syringe. The vessel was pressurized to 40 psi and shaken in a Parr shaker for ˜24 h. The resulting material was flushed with nitrogen and filtered through Celite, rinsing with MeOH. The filtrate was concentrated in vacuo to give 2-amino-4-benzylphenol as a brown solid. MS (ESI) m/z: Calculated: 199.1; Observed: 200.0 (M++1). delivered via syringe The resulting material was flushed with nitrogen filtered through Celite rinsing with MeOH The filtrate was concentrated in vacuo