Oxalyl chloride → (E)-2-(6-fluoro-1-indanylidene)acetyl chloride

HRID 862761Notes

Reaction equation

HRID 862761 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7]/[C:8]/2=[CH:11]\[C:12]([OH:14])=O)=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:18])=O>C1C=CC=CC=1>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7]/[C:8]/2=[CH:11]\[C:12]([Cl:18])=[O:14])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 70130971(E)-2-(6-fluoro-1-indanylidene)acetic acid

Product 1

HCID 15491026(E)-2-(6-fluoro-1-indanylidene)acetyl chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

An ice-cold, stirred suspension of (E)-2-(6-fluoro-1-indanylidene) acetic acid (384 mg, 2 mmol) in benzene (10 mL) was treated with oxalyl chloride (761 mg, 6 mmol) and allowed to warm to room temperature during 1.5 h. The resulting yellow solution was concentrated in vacuo to give (E)-2-(6-fluoro-1-indanylidene)acetyl chloride as a pale yellow solid (421 mg, 100%), m.p., 97°-99° C.; IR (Nujol (high boiling petroleum oil)): 1750, 1600 cm-1 ; NMR (DMSO-d6): d 7.18-7.67 (m, 3H, Ar), 6.39 (t, 1H, =CH), 2.96-2.99, 3.16-3.21 (2m's, 4H, 2XCH2).

Workup

  1. concentrationThe resulting yellow solution was concentrated in vacuo

Sources & evidence

ORD record
ord-250936427c6841358ed61df76f2cedca
Source dataset
uspto-grants-1998_02
Patent number
US05719186

Reaction notes

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