Sodium Chloride → methyl N-[5-(3,3-dimethyl-1-butynyl)-2-fluorobenzyl]carbamate

HRID 427243Notes

Reaction equation

HRID 427243 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].[CH3:15][C:16]([CH3:20])([CH3:19])[C:17]#[CH:18].C(N(CC)CC)C.[Cl-].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.CN(C)C=O>[CH3:15][C:16]([CH3:20])([CH3:19])[C:17]#[C:18][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]

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 135123,3-Dimethyl-1-butyneHCID 15483912methyl N-(5-bromo-2-fluorobenzyl)carbamate

Product 1

HCID 15483913methyl N-[5-(3,3-dimethyl-1-butynyl)-2-fluorobenzyl]carbamateYield 39.8%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture comprising 1.00 g of methyl N-(5-bromo-2-fluorobenzyl)carbamate, 0.75 g of 3,3-dimethyl-1-butyne, 0.06 g of dichlorobis(triphenylphosphine)palladium, 0.02 g of copper(I) iodide, 1.29 g of triethylamine and 2.7 ml of N,N-dimethylformamide, was stirred at room temperature for 48 hours in a nitrogen atmosphere. This reaction solution was poured into a saturated sodium chloride aqueous solution and extracted with ethyl acetate, followed by 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 0.40 g of methyl N-[5-(3,3-dimethyl-1-butynyl)-2-fluorobenzyl]carbamate as brown crystals.

Workup

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

Sources & evidence

ORD record
ord-3f0c2f6efbc44843bea87ed9a11d50b0
Source dataset
uspto-grants-2001_11
Patent number
US06313071B1

Reaction notes

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