Water → 2,4-Dichloro-6-fluorobenzonitrile

HRID 1481327Notes

Reaction equation

HRID 1481327 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([F:12])[C:3]=1[C:4]([NH2:6])=O.CCN(CC)CC.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O.O>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([F:12])[C:3]=1[C:4]#[N:6]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 224781602,4-Dichloro-6-fluorobenzamide

Product 1

HCID 566042552,4-Dichloro-6-fluorobenzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,4-dichloro-6-fluorobenzamide (5.07 mmol) (US 20060178386) in 74 mL DCM were added Et3N (15.2 mmol) followed by TFAA (10.1 mmol) at 0° C. After 30 min, water was added, the organic layer was separated and concentrated in vacuo. Purification with CC (KP-SIL™ from Biotage) using Hept/EtOAc ( 4/1 to ⅓) gives the desired compound as colorless solid.

Workup

  1. customthe organic layer was separated
  2. concentrationconcentrated in vacuo
  3. customPurification with CC (KP-SIL™ from Biotage)

Sources & evidence

ORD record
ord-51a6f22e51b14da2a8ef772e6f8e3a23
Source dataset
uspto-grants-2016_08
Patent number
US09409917B2

Reaction notes

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