Water → 4-((4-Chlorophenyl)thio)-5,8-difluorochroman-3-ol

HRID 564319Notes

Reaction equation

HRID 564319 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]2[C:3]=1[CH:4]1[O:13][CH:5]1[CH2:6][O:7]2.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([SH:21])=[CH:17][CH:16]=1.O>C(Cl)Cl>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([S:21][CH:4]2[C:3]3[C:8](=[C:9]([F:12])[CH:10]=[CH:11][C:2]=3[F:1])[O:7][CH2:6][CH:5]2[OH:13])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7815p-ChlorothiophenolHCID 552675294,7-difluoro-2,7b-dihydro-1aH-oxireno[2,3-c]chromene

Product 1

HCID 584453284-((4-Chlorophenyl)thio)-5,8-difluorochroman-3-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5,8-Difluoro-2H-chromene oxide (23 g, 0.125 mole) and 4-Chloro-benzenethiol (18.1 g, 0.125 mmole) were dissolved in 500 ml DCM and InCl3 (2.9 g, 0.013 mole) was added. The reaction was stirred at room temperature overnight. 200 ml DCM and 200 ml water were added. The organic layer washed with brine, dried over Na2SO4 and concentrated. The product was purified by column chromatography (EtOAc/hexane from 0/100 to 50/50 in 55 minute). Yield: 23.2 g, 57%. 1H NMR (CDCl3 400 MHz δ 7.48 (d, J=8.8 Hz, 2H), 7.34 (d, J=8.8 Hz, 2H), 7.01 (m, 1H), 6.64 (m, 1H), 4.63 (d, J=11.7 Hz, 1H), 4.32-4.41 (m, 2H), 4.12 (m, 1H).

Workup

  1. washThe organic layer washed with brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe product was purified by column chromatography (EtOAc/hexane from 0/100 to 50/50 in 55 minute)

Sources & evidence

ORD record
ord-a1f321978fe4431dba397d933b456dee
Source dataset
uspto-grants-2011_11
Patent number
US08067621B2

Reaction notes

Loading…