Water → HCID 67241298, compound

HRID 1970298Notes

Reaction equation

HRID 1970298 reaction equation
[Br:1][C:2]1[CH:15]=[C:14]2[C:5]([O:6][C:7]3[CH:8]=[C:9](F)[C:10]([F:17])=[CH:11][C:12]=3[C:13]2=[O:16])=[CH:4][CH:3]=1.[F:19][C:20]([F:24])([F:23])[CH2:21][OH:22].[H-].[Na+].O>CN(C=O)C>[Br:1][C:2]1[CH:15]=[C:14]2[C:5]([O:6][C:7]3[CH:8]=[C:9]([O:22][CH2:21][C:20]([F:24])([F:23])[F:19])[C:10]([F:17])=[CH:11][C:12]=3[C:13]2=[O:16])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 58466288HCID 58466288, compound

Product 1

HCID 67241298HCID 67241298, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-bromo-2,3-difluoro-9H-xanthen-9-one (3.1 g, 9.97 mmol) and 2,2,2-trifluoroethanol (1.445 mL, 19.93 mmol) in DMF (33 mL) at 0° C. was added sodium hydride (0.598 g, 14.95 mmol) slowly in portions. After addition, the mixture was stirred at RT for overnight. Then, H2O (100 mL) was added slowly and the mixture was extracted with EtOAc (1×100 mL). The organic layer was collected, dried over MgSO4, and concentrated. The residue was then washed with hexane (1×100 mL) to give 2.76 g of 7-bromo-2-fluoro-3-(2,2,2-trifluoroethoxy)-9H-xanthen-9-one as a light yellow solid. MS (ESI, positive ion) m/z: 390.9, 392.9 (M+1).

Workup

  1. additionAfter addition
  2. extractionthe mixture was extracted with EtOAc (1×100 mL)
  3. customThe organic layer was collected
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. washThe residue was then washed with hexane (1×100 mL)

Sources & evidence

ORD record
ord-8b0f0d260d57474cbea58f1ec0c62a6e
Source dataset
uspto-grants-2013_04
Patent number
US08426447B2

Reaction notes

Loading…