p-Toluenesulfonic acid → HCID 18412754, compound

HRID 992487Notes

Reaction equation

HRID 992487 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[SH:9].C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:21]1[CH:26]=[CH:25][CH2:24][CH2:23][CH2:22]1.[OH-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9][CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][O:21]1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 14798Sodium HydroxideHCID 218168372-Bromo-4-chlorobenzene-1-thiol

Product 1

HCID 18412754HCID 18412754, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of 2-bromo-4-chlorothiophenol (3.74 g, 16.8 mmol), p-toluene sulfonic acid (0.427 g, 1.7 mmol) and 3,4-dihydro-2-H-pyran (0.985 ml, 16.8 mmol) in CH2Cl2 (30 mL) was stirred at 23° C. for 18 hours. After the addition of NaOH, the organic phase was separated, dried over MgSO4, filtered and the filtrate was concentrated in vacuo to afford the title compound as a yellow oil, (4.91 g, 95%) 1H NMR (CDCl3) δ7.6-7.5 (m, 2H), 7.35-7.2 (m, 1H), 5.37 (t, J=4.5 Hz, SCHO, 1H), 4.25-4.1 (m, CH2O, 1H), 3.7-3.55 (m, CH2O, 1H), 2.2-2.05 (m, 1H), 2.0-1.8 (m, 2H), 1.8-1.6 (m, 3H): IR 1566, 1542, 1450, 1367, 1257, 1188, 1101, 1037, 1024, 1008, 867, 809, 783 cm−1; Anal. Calcd. for C11H12BrClOS: C, 42.95; H, 3.93. Found: C,43.15; H, 3.91.

Workup

  1. customthe organic phase was separated
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-897ab0261271463db520088905501608
Source dataset
uspto-grants-2002_10
Patent number
US06469042B1

Reaction notes

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