Bromine → HCID 178517592, compound

HRID 1820983Notes

Reaction equation

HRID 1820983 reaction equation
[OH:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[Br:12]Br>CO>[OH:1][C:2]1[C:7]([C:8]([F:9])([F:11])[F:10])=[CH:6][C:5]([Br:12])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 36784112(1H)-Pyridinone, 3-(trifluoromethyl)-

Product 1

HCID 178517592HCID 178517592, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.95 g (12 mmol) of 2-hydroxy-3-trifluoromethyl-pyridine and 0.8 mL of bromine in 10 mL of MeOH was stirred at rt for 20 h. The solution was concentrated and the residue partitioned between 100 mL of EtOAc and 25 mL of H2O. The layers were separated and the organic layer was washed with 25 mL of 5% Na2S2O3, 25 mL of sat'd NaCl, dried and concentrated. Chromatography on a Biotage 40 M cartridge using 3:1 hexanes/acetone as the eluant afforded 1.84 g of the title compound: ESI-MS (m/z) 242.1, 244.1; HPLC A: 2.22 min.

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue partitioned between 100 mL of EtOAc and 25 mL of H2O
  3. customThe layers were separated
  4. washthe organic layer was washed with 25 mL of 5% Na2S2O3, 25 mL of sat'd NaCl
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a1198ba4a9bd40d5888d36d39826f2f7
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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