Pyridine → Phenyl (3-fluoro-4-(hydroxymethyl)phenyl)carbamate

HRID 1843045Notes

Reaction equation

HRID 1843045 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4]([F:10])[CH:3]=1.N1C=CC=CC=1.Cl[C:18]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19]>CC(C)=O>[F:10][C:4]1[CH:3]=[C:2]([NH:1][C:18](=[O:19])[O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:7]=[CH:6][C:5]=1[CH2:8][OH:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 45116731(4-Amino-2-fluorophenyl)methanol

Product 1

HCID 86672140Phenyl (3-fluoro-4-(hydroxymethyl)phenyl)carbamateYield 60%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of (4-amino-2-fluorophenyl)methanol (100 mg, 0.709 mmol, 1 eq.) in acetone (1.0 mL) was added pyridine (0.17 mL, 2.12 mmol, 3 eq.) followed by phenyl chloroformate (0.092 mL, 0.709 mmol, 1 eq.) at 0° C. and stirred at RT for 1 h. The solvent was evaporated and the residue obtained was purified by CC using ethyl acetate/PE (7:13) as eluent to get phenyl 3-fluoro-4-(hydroxymethyl)phenylcarbamate (110 mg, 60%, off-white solid; TLC system: EtOAc/PE (1:1), Rf: 0.4).

Workup

  1. customThe solvent was evaporated
  2. customthe residue obtained
  3. customwas purified by CC

Sources & evidence

ORD record
ord-59b18729b944470cadff20a5272cf258
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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