Hydrochloric Acid → 7,8-Difluoro-5-iodochroman-6-ol
Reaction equation
Cl.[F:2][C:3]1[C:12]([F:13])=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][O:10]2)=[C:5]([I:14])[C:4]=1[O:15]COC>C1COCC1.CC(OC)(C)C>[F:2][C:3]1[C:12]([F:13])=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][O:10]2)=[C:5]([I:14])[C:4]=1[OH:15]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 20 °C
Procedure
10.4 ml of conc. HCl are added to a solution of 20.2 g (56.7 mmol) of 7,8-difluoro-5-iodo-6-methoxymethoxychroman in 100 ml of THF, and the mixture is stirred at 20° C. for 18 h. The batch is diluted with MTBE, and the solution is washed with water. The aqueous phase is extracted with MTBE, and the combined organic phases are washed with water and sat. sodium chloride soln. The solution is dried using sodium sulfate and concentrated to dryness. The crude product is purified by column chromatography (SiO2, n-heptane:MTBE=1:1), giving 7,8-difluoro-5-iodochroman-6-ol as a pale-brown solid.
Workup
- washthe solution is washed with water
- extractionThe aqueous phase is extracted with MTBE
- washthe combined organic phases are washed with water and sat. sodium chloride soln
- customThe solution is dried
- concentrationconcentrated to dryness
- customThe crude product is purified by column chromatography (SiO2, n-heptane:MTBE=1:1)
Sources & evidence
- ORD record
- ord-b49d028589aa458583fe490e956e7f40
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07678929B2
Reaction notes
Loading…