Hydrogen Bromide → HCID 19426970, compound

HRID 260443Notes

Reaction equation

HRID 260443 reaction equation
[BrH:1].N[C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:14]([F:17])([F:16])[F:15])=[CH:8][C:9](=[O:13])[O:10]2)=[CH:5][CH:4]=1.N([O-])=O.[Na+]>O>[Br:1][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:14]([F:17])([F:16])[F:15])=[CH:8][C:9](=[O:13])[O:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 1006417-Amino-4-(trifluoromethyl)coumarinHCID 23668193Sodium Nitrite

Product 1

HCID 19426970HCID 19426970, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 48% HBr (4.5 g, 26.7 mmol) (3 mL) containing 7-amino-4-trifluoromethylcoumarin (Aldrich) (2.0 g, 8.8 mmol) at -10° C. was added NaNO2 (670 mg in 1 mL of H2O) then Cu powder 35 mg was added. The reaction mixture was stirred at r.t. for 30 min., then heated to 100° C. for 30 min. The reaction mixture was cooled to 0° C. and H2O (25 mL) was added. The mixture was extracted with EtOAc (400 mL) and the combined organic phase was washed with brine (200 mL) dried over MgSO4 and evaporated. The crude solid was purified by chromatography on silica gel using hexane:EtOAc 8:2 as eluent, to give 1.5 g (58%) of the title compound as a white solid.

Workup

  1. temperatureheated to 100° C. for 30 min
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. extractionThe mixture was extracted with EtOAc (400 mL)
  4. washthe combined organic phase was washed with brine (200 mL)
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customThe crude solid was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-588a8bfd7c7d43c5ace348fd5a541479
Source dataset
uspto-grants-1996_06
Patent number
US05527827

Reaction notes

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