Oxalyl chloride → Bicyclo[2.2.2]oct-2-ene-2-carbonyl chloride

HRID 8076Notes

Reaction equation

HRID 8076 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[CH:7]12[CH2:14]C[CH:10]([CH2:11][CH2:12]1)[CH:9]=[C:8]2C(O)=O>C(Cl)Cl.CN(C=O)C>[CH:10]12[CH2:11][CH2:12][CH:7]([CH2:8][CH2:9]1)[CH:14]=[C:1]2[C:2]([Cl:4])=[O:3]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 22014830Bicyclo[2.2.2]oct-2-ene-2-carboxylic acid

Product 1

HCID 22014823Bicyclo[2.2.2]oct-2-ene-2-carbonyl chlorideYield 100.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (2.0 M in CH2Cl2, 2.4 mL, 4.8 mmol, 1.2 eq) was added to a solution of compound 11B (600 mg, 3.95 mmol, 1 eq) in CH2Cl2 (8 mL) containing one drop of DMF. The reaction mixture was stirred at rt for 3 h and then concentrated under reduced pressure to give 680 mg of compound 11C which was used in the next step without purification. D. Bicyclo[2.2.2]oct-2-ene-2-carboxylic acid (4-nitro-3-trifluoromethylphenyl)-amide (11D)

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1909c0ad6b5f4b5bb7d6bc3e0ee986fa
Source dataset
uspto-grants-2006_08
Patent number
US07087636B2

Reaction notes

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