Thionyl Chloride → HCID 2773933, compound

HRID 2189147Notes

Reaction equation

HRID 2189147 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[F:12])[C:6](O)=[O:7])#[N:2].S(Cl)([Cl:15])=O>>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[F:12])[C:6]([Cl:15])=[O:7])#[N:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 27739323-Cyano-4-fluorobenzoic acid

Product 1

HCID 2773933HCID 2773933, compoundYield 99.7%

Conditions

Temperature
80 °C

Procedure

In a 250 mL round bottom flask a mixture of 3-cyano-4-fluorobenzoic acid (7.75 g, 0.047 mol) and thionyl chloride (28 mL, 0.38 mol, 8 eq) was heated to 80° C. for 1 h. The reaction mixture was concentrated in vacuo to give 8.6 g of 3-cyano-4-fluorobenzoyl chloride which can be used in the next step without further purification. 1H NMR (400 MHz, CDCl3): δ 8.49-8.43 (m, 1H), 8.42-8.36 (m, 1H), 7.44 (t, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-7c47aa6ab83c467eaed6044c8b4ec0b1
Source dataset
uspto-grants-2012_12
Patent number
US08324231B2

Reaction notes

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