Oxalyl chloride → HCID 23293589, compound

HRID 1954900Notes

Reaction equation

HRID 1954900 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:16])([CH3:15])[CH2:7]/[C:8]/2=[CH:11]\[C:12](O)=[O:13])=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:20])=O>ClCCl>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:16])([CH3:15])[CH2:7]/[C:8]/2=[CH:11]\[C:12]([Cl:20])=[O:13])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 23293609Acetic acid, (6-fluoro-2,3-dihydro-3,3-dimethyl-1H-inden-1-ylidene)-, (2E)-

Product 1

HCID 23293589HCID 23293589, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To an ice cold, stirred suspension of (E)-2-(6-fluoro-3,3-dimethyl-1-indanylidene)acetic acid (9.0 g, 0.0409 mol) in dichloromethane (200 ml) was added oxalyl chloride (15.6 g, 0.123 mol, Aldrich). The stirring suspension was allowed to warm to 25° C. during 2 h. The resulting solution was concentrated by spin evaporation in vacuo with the addition of dichloromethane (4×75 ml) to give (E)-2-(6-fluoro-3,3-dimethyl-1-indanylidene)acetyl chloride as an uncharacterized oil. Dichloromethane (approximately 70 g) was added to dissolve this residual oil and the resulting solution was divided equally and used without other purification in Examples 15i, 16 and 17.

Workup

  1. concentrationThe resulting solution was concentrated by spin evaporation in vacuo with the addition of dichloromethane (4×75 ml)

Sources & evidence

ORD record
ord-ad57b52361464173af6b0ab894caef4a
Source dataset
uspto-grants-2000_09
Patent number
US06124284

Reaction notes

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