Sodium Bicarbonate → 7-Bromo-4,4-dimethylthiochroman

HRID 899275Notes

Reaction equation

HRID 899275 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8][CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12])[CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([C:11]([CH3:13])([CH3:12])[CH2:10][CH2:9][S:8]2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 22640690m-Bromophenyl 3-methyl-2-butenyl sulfide

Product 1

HCID 223930997-Bromo-4,4-dimethylthiochromanYield 86.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of 1-bromo-3-(3-methyl-but-2-enylsulfanyl)-benzene (5.651 g, 22 mmole) in 100 mL of toluene was treated with 5.433 g of p-toluenesulfonic acid monohydrate and heated at reflux for 15 hours. The mixture was diluted with 100 mL of water, neutralized with solid sodium bicarbonate and extracted with two 100 mL portions of ethyl acetate. The organic phase was dried over MgSO4, filtered and concentrated in vacuo to give a yellow oil. The product was purified by short path distillation (T=190° C. at 1.08 Torr) to give 4.902 g of 7-bromo-4,4-dimethyl-thiochroman as a pale yellow oil, which contained approximately 20% 5-bromo-4,4-dimethyl-thiochroman.

Workup

  1. temperatureheated
  2. temperatureat reflux for 15 hours
  3. extractionextracted with two 100 mL portions of ethyl acetate
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a yellow oil
  8. distillationThe product was purified by short path distillation (T=190° C. at 1.08 Torr)

Sources & evidence

ORD record
ord-7f5874c302d1406197f2a223c30302c2
Source dataset
uspto-grants-2008_04
Patent number
US07354931B2

Reaction notes

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