1,4-Dioxane → HCID 11436666, compound

HRID 1755088Notes

Reaction equation

HRID 1755088 reaction equation
[F:1][C:2]1([F:14])[O:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[O:4][C:3]1([F:13])[F:12].[B:15]1(B2OC(C)(C)C(C)(C)O2)[O:19]C(C)(C)C(C)(C)[O:16]1.O1CCOCC1.I(O)(=O)(=O)=O>O.CO>[F:13][C:3]1([F:12])[O:4][C:5]2[CH:11]=[CH:10][C:9]([B:15]([OH:19])[OH:16])=[CH:8][C:6]=2[O:7][C:2]1([F:1])[F:14]

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 65185Metaperiodic acidHCID 2733548Bis(pinacolato)diboraneHCID 27765882,2,3,3-Tetrafluoro-2,3-dihydro-1,4-benzodioxine

Product 1

HCID 11436666HCID 11436666, compoundYield 78.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

2,2,3,3-Tetrafluoro-1,4-benzodioxane (484 mg), bis(pinacolato)diboron (295 mg), [Ir(COD)(OMe)]2 (15.4 mg) and 4,4′di-tert-butyl-2,2′-dipyridyl (12.5 mg) were mixed. 1,4-Dioxane (0.5 mL) was added in a nitrogen atmosphere and stirred at 100° C. for two hours. MeOH (0.5 mL) was added to the reaction solution, and metaperiodic acid (1.06 g) was added in four portions under ice-cooling. Water was added to the reaction solution, followed by extraction with ethyl acetate and concentration. The resulting mixture was purified by silica gel column chromatography to give 2,2,3,3-tetrafluoro-2,3-dihydro-benzo[1,4]dioxin-6-yl-boronic acid (230 mg, 39%).

Workup

  1. additionwas added in four portions under ice-
  2. temperaturecooling
  3. extractionfollowed by extraction with ethyl acetate and concentration
  4. customThe resulting mixture was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f2bcd5278b634360a83ce212c2dcb7c8
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

Loading…