2,6-Difluorobenzyl alcohol → HCID 117858781, compound

HRID 1486311Notes

Reaction equation

HRID 1486311 reaction equation
CC(C)([O-])C.[K+].[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[C:9]=1[CH2:15][OH:16].[Br:17][C:18]1[CH:23]=[CH:22][N:21]=[C:20](F)[CH:19]=1>O1CCCC1>[Br:17][C:18]1[CH:23]=[CH:22][N:21]=[C:20]([O:16][CH2:15][C:9]2[C:8]([F:7])=[CH:13][CH:12]=[CH:11][C:10]=2[F:14])[CH:19]=1

Participants

5

Reactant 3

HCID 879212,6-Difluorobenzyl alcoholHCID 27628514-Bromo-2-fluoropyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 117858781HCID 117858781, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

15.5 ml (15.5 mmol) of a 1 M solution of potassium tert-butoxide in tetrahydrofuran was added dropwise at 0° C. to a solution of 1.72 ml (15.5 mmol) of (2,6-difluorophenyl)methanol and 1.6 ml (15.5 mmol) of 4-bromo-2-fluoropyridine in 50 ml of anhydrous tetrahydrofuran. The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was partitioned between ethyl acetate and water. The organic phase was removed and washed with water and saturated aqueous sodium chloride solution, dried over sodium sulphate, filtered and concentrated. The residue was purified by chromatography on silica gel (40 g silica gel cartridge, mobile phase: cyclohexane/ethyl acetate, gradient 0% to 100%). This gave 4.12 g of the target compound (88% of theory).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. customThe organic phase was removed
  3. washwashed with water and saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel (40 g silica gel cartridge, mobile phase: cyclohexane/ethyl acetate, gradient 0% to 100%)

Sources & evidence

ORD record
ord-099528463e5f42e6a9639f4c5c017acd
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

Loading…