Trifluoroacetic acid → HCID 71255617, compound

HRID 1508328Notes

Reaction equation

HRID 1508328 reaction equation
[N:1]([C:4]1[C:9]([F:10])=[C:8]([Cl:11])[CH:7]=[CH:6][C:5]=1[F:12])=[N+:2]=[N-:3].Cl[C:14]1C(F)=C(C(F)=C[CH:20]=1)N.N([O-])=O.[Na+].[N-]=[N+]=[N-].[Na+].[C:31]([OH:37])([C:33](F)(F)F)=[O:32]>O>[Cl:11][C:8]1[C:9]([F:10])=[C:4]([N:1]2[C:14]([CH3:20])=[C:33]([C:31]([OH:37])=[O:32])[N:3]=[N:2]2)[C:5]([F:12])=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 33557Sodium AzideHCID 177507453-Chloro-2,6-difluoroanilineHCID 23668193Sodium NitriteHCID 89406114HCID 89406114, compound

Product 1

HCID 71255617HCID 71255617, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

2-Azido-4-chloro-1,3-difluorobenzene: To a solution of 3-chloro-2,6-difluoroaniline (1.7 g, 10.39 mmol) in TFA (10 mL) and water (2 mL) at 0° C. was added sodium nitrite (0.717 g, 10.39 mmol) over a period of 0.5 h. After completion of addition, sodium azide (1.716 g, 26.4 mmol) in water (5 mL) was added dropwise. The reaction mixture was stirred at 0° C. for 10 min and then allowed to warm to rt. The reaction was diluted with water (75 mL) and extracted with EtOAc. The organic layer was dried and concentrated to give the desired product (1.16 g, 56%) as a brown solid.

Workup

  1. additionwas added dropwise
  2. temperatureto warm to rt
  3. extractionextracted with EtOAc
  4. customThe organic layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-144d3d9a220a4a3486c1abd7d4706fa8
Source dataset
uspto-grants-2015_12
Patent number
US09221818B2

Reaction notes

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