Thionyl Chloride → HCID 17851141, compound

HRID 11238Notes

Reaction equation

HRID 11238 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][C:7]2[O:11][C:10]([C:12](O)=[O:13])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.S(Cl)([Cl:19])=O>CN(C=O)C>[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][C:7]2[O:11][C:10]([C:12]([Cl:19])=[O:13])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21972640HCID 21972640, compound

Product 1

HCID 17851141HCID 17851141, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 5-(4-fluorobenzyl)-2-furan carboxylic acid (450 mg, 2 mmol) were added thionylchloride (1 ml, 13.7 mmol) and DMF (0.025 ml). The mixture was stirred for 30 minutes at room temperature. The excess amount of thionylchloride was evaporated. The precipitated residue was washed with n-hexane to give crude 5-(4-fluorobenzyl)-2-furan carboxylic acid chloride (480 mg). NMR(CDCl3) δ: 4.03(2H, s), 6.20(1H, d, J=3.6 Hz), 7.03(2H, t, J=8.7 Hz), 7.19-7.24(2H, m), 7.42(1H, d, J=3.6 Hz).

Workup

  1. customThe excess amount of thionylchloride was evaporated
  2. washThe precipitated residue was washed with n-hexane

Sources & evidence

ORD record
ord-6991e5618fb54c83871f08fecd22030d
Source dataset
uspto-grants-2006_08
Patent number
US07098201B2

Reaction notes

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