Potassium Carbonate → HCID 86683211, compound

HRID 1852136Notes

Reaction equation

HRID 1852136 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[C:17]2[C:12](=[C:13]([Cl:18])[CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]([OH:19])[N:9]=1.Br[CH2:21][CH:22]([F:24])[F:23]>O>[Cl:7][C:8]1[C:17]2[C:12](=[C:13]([Cl:18])[CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]([O:19][CH2:21][CH:22]([F:24])[F:23])[N:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1361862-Bromo-1,1-difluoroethaneHCID 178515367HCID 178515367, compound

Product 1

HCID 86683211HCID 86683211, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Potassium carbonate (646 mg, 4.67 mmol) was added to a solution of 1,5-dichloroisoquinolin-3-ol (500 mg, 2.336 mmol) and 2-bromo-1,1-difluoroethane (677 mg, 4.67 mmol) and heated to 50° C. for 18 hrs. The reaction was diluted with water and extracted with EtOAc. The organic layer was washed with water (2×) followed by brine. The organic layer was collected, dried over MgSO4, filtered and evaporated to give the crude product 1,5-dichloro-3-(2,2-difluoroethoxy)isoquinoline (590 mg, 90% yield) which was used as is in the next step. MS: MS m/z 278.1(M++1).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with water (2×)
  3. customThe organic layer was collected
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-6a8e0be3aab84de2952abefe1d06b464
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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