Potassium Carbonate → 4-(4-Bromophenyl)sulfanyltetrahydropyran

HRID 869038Notes

Reaction equation

HRID 869038 reaction equation
I[CH:2]1[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([SH:15])=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOCC>[Br:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][CH:2]2[CH2:7][CH2:6][O:5][CH2:4][CH2:3]2)=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 660494-BromothiophenolHCID 27955064-iodotetrahydro-2H-pyran

Product 1

HCID 188010624-(4-Bromophenyl)sulfanyltetrahydropyranYield 85.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

4-Iodotetrahydropyran (9 g, 42.45 mmol) was added to a stirred suspension of 4-bromobenzenethiol (7.296 g, 38.59 mmol) and potassium carbonate (10.67 g, 77.18 mmol) in DMF (15 mL) and the reaction stirred at ambient temperature for 3 hours. The mixture was diluted with Et2O and washed with water (×2) and brine (×1). The organic extracts was dried (MgSO4) and concentrated in vacuo. Petroleum ether was added to the residue and the resultant precipitate removed by filtration. The filtrate was concentrated in vacuo to give the sub-title compound as a light yellow oil (9.0 g, 85% Yield). 1H NMR (400.0 MHz, CDCl3) δ 1.63-1.73 (m, 2H), 1.89-1.93 (m, 2H), 3.23-3.30 (m, 1H), 3.45 (td, 2H), 3.99 (dt, 2H), 7.31 (d, 2H) and 7.45 (d, 2H) ppm.

Workup

  1. washwashed with water (×2) and brine (×1)
  2. dry with materialThe organic extracts was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. additionPetroleum ether was added to the residue
  5. customthe resultant precipitate removed by filtration
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-bedc8b05105b402c83c59fe5f3f985d8
Source dataset
uspto-grants-2015_03
Patent number
US08969356B2

Reaction notes

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