Benzyl Alcohol → benzyl N-[(4-bromo-2-fluorophenyl)methyl]carbamate

HRID 1204

Reaction equation

HRID 1204 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:9]([C:11]#[N:12])[K].[Br:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[C:16]([F:22])[CH:15]=1>CN(C=O)C>[Br:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][NH:12][C:11](=[O:9])[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:16]([F:22])[CH:15]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 27336604-Bromo-2-fluorobenzyl bromideHCID 178418250HCID 178418250, compound

Product 1

HCID 19695037benzyl N-[(4-bromo-2-fluorophenyl)methyl]carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

Anhydrous and amine-free DMF (180 ml) and benzyl alcohol (28 ml) and KOCN (0.247 mol, 20 g) are charged into a 500 ml 2-neck round bottom flask having a reflux condenser and drying tube. A solution of 4-bromo-2-fluorobenzyl bromide (0.075 mol, 20 g) in DMF (20 ml) is added rapidly (in the course of 1 min) at room temperature to the stirred reaction mixture by means of a dropping funnel. The resulting suspension is subsequently heated with stirring to approximately 110° C. and further stirred at this temperature for approximately 1.5 h. The mixture is then cooled to room temperature. The salt present in the reaction mixture is filtered off by suction via a frit. The solvent and excess benzyl alcohol are removed from the filtrate in vacuo. The light yellow oily residue is cooled with ice for crystallization. The bright crystalline mass produced is washed with water, filtered and dried. Yield: 23.2 g (:91.5% of theory) M.p.: 82°-84° C. GC/MS: M+ =337, IR in KBr [cm-1 ]: 3342 (m) N--H, 1689 (s) C=O, 1535 (m) NH--C, 1276 (m) C--O--C

Workup

  1. customdrying tube
  2. customto the stirred reaction mixture by means of a dropping funnel
  3. temperatureThe resulting suspension is subsequently heated
  4. stirringfurther stirred at this temperature for approximately 1.5 h
  5. temperatureThe mixture is then cooled to room temperature
  6. filtrationThe salt present in the reaction mixture is filtered off by suction via a frit
  7. customThe solvent and excess benzyl alcohol are removed from the filtrate in vacuo
  8. temperatureThe light yellow oily residue is cooled with ice for crystallization
  9. customThe bright crystalline mass produced
  10. washis washed with water
  11. filtrationfiltered
  12. customdried

Sources & evidence

ORD record
ord-440b49e065434692a260e63870f36ce7
Source dataset
uspto-grants-1998_03
Patent number
US05723647

Linked notes

Loading…