Sodium Chloride → methyl N-[2-fluoro-5-(3-hydroxy-1-butynyl)benzyl]carbamate

HRID 427241Notes

Reaction equation

HRID 427241 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:14])=[C:6]([CH:13]=1)[CH2:7][NH:8][C:9](=[O:12])[O:10][CH3:11].[CH:15]#[C:16][CH:17]([OH:19])[CH3:18].[Cl-].[Na+]>[Cu]I.C(N(CC)CC)C>[F:14][C:5]1[CH:4]=[CH:3][C:2]([C:15]#[C:16][CH:17]([OH:19])[CH3:18])=[CH:13][C:6]=1[CH2:7][NH:8][C:9](=[O:12])[O:10][CH3:11]

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 162393-Butyn-2-olHCID 15483912methyl N-(5-bromo-2-fluorobenzyl)carbamate

Product 1

HCID 15483914methyl N-[2-fluoro-5-(3-hydroxy-1-butynyl)benzyl]carbamateYield 41.1%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
100 °C

Procedure

A mixture comprising 1.60 g of methyl N-(5-bromo-2-fluorobenzyl)carbamate, 1.40 g of 1-butyn-3-ol, 0.20 g of palladium dichlorobis(triphenylphosphine), 0.10 g of copper(I) iodide and 10 ml of triethylamine, was stirred at 100° C. for 48 hours in an autoclave. The reaction solution was poured into a saturated sodium chloride aqueous solution and extracted with ethyl acetate, followed by washing with water and drying over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 0.63 g of methyl N-[2-fluoro-5-(3-hydroxy-1-butynyl)benzyl]carbamate as a brown viscous liquid.

Workup

  1. extractionextracted with ethyl acetate
  2. washby washing with water
  3. dry with materialdrying over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d5be83816bf040c9bd7574454982fef2
Source dataset
uspto-grants-2001_11
Patent number
US06313071B1

Reaction notes

Loading…