3-Chloro-2-methyl-1-propene → HCID 22905880, compound

HRID 2257255Notes

Reaction equation

HRID 2257255 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([CH3:11])([CH3:10])[CH3:9])[C:3]=1[SH:12].C([O-])([O-])=O.[K+].[K+].N[C@H](C(O)=O)[CH2:21][C:22]1[CH:31]=C2C(C=CC=C2)=C[CH:23]=1.ClCC(C)=C>CC(C)=O>[CH:21]([S:12][C:3]1[C:4]([C:8]([CH3:9])([CH3:11])[CH3:10])=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1])=[C:22]([CH3:31])[CH3:23]

Participants

6

Reactant 4

HCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium CarbonateHCID 1859152-NaphthylalanineHCID 107528662-bromo-6-tert-butylthiophenol

Product 1

HCID 22905880HCID 22905880, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
24 °C

Procedure

A mixture of 2-bromo-6-tert-butylthiophenol (6.04 g, 22.7 mmol), K2CO3 (3.76 g, 27.2 mmol), Nal (0.34 g, 2.27 mmol), and 3-chloro-2-methylpropene (2.3 mL, 22.7 mmol) in acetone (125 mL) is heated at reflux for 3 h. The reaction is allowed to cool to 24° C. The solids are filtered and discarded, and the filtrate is evaporated to a biphasic oil. The upper light colored layer is separated, taken up in hexane (50 mL), and treated with SiO2 (5 g). Filtration and evaporation provides 2-bromo-6-tert-butylphenyl isobutenyl thioether as a yellow oil.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 3 h
  3. filtrationThe solids are filtered
  4. customthe filtrate is evaporated to a biphasic oil
  5. customThe upper light colored layer is separated
  6. additiontreated with SiO2 (5 g)
  7. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-85b6562227f34c5aaa2e478dac3ee214
Source dataset
uspto-grants-1997_08
Patent number
US05656661

Reaction notes

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