Dimethylformamide → Bicyclo(2.2.1)hept-5-ene-2-carbonyl chloride

HRID 1853415Notes

Reaction equation

HRID 1853415 reaction equation
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[C:8]([OH:10])=O.C(Cl)(=O)C([Cl:14])=O.CN(C)C=O>ClCCl>[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[C:8]([Cl:14])=[O:10]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 789495-Norbornene-2-carboxylic acid

Product 1

HCID 98233Bicyclo(2.2.1)hept-5-ene-2-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-norbornene-2-carboxylic acid (Aldrich, mixture of endo and exo, 1.25 g, 9.05 mmol) in dichloromethane (50 mL) was treated with oxalyl chloride (0.99 mL, 11.31 mmol) and a catalytic amount of N,N-dimethylformamide (100 μL). The reaction mixture was stirred at ambient temperature for 2 hours and then solvent and excess oxalyl chloride were removed under reduced pressure to yield the title compound which was used without further purification.

Workup

  1. customsolvent and excess oxalyl chloride were removed under reduced pressure

Sources & evidence

ORD record
ord-9cab44db8f444fe581815f7e34a0103e
Source dataset
uspto-grants-2015_02
Patent number
US08962639B2

Reaction notes

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