1,1-Dibromoethane → HCID 20484457, compound

HRID 648063Notes

Reaction equation

HRID 648063 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[C:9]([S:11]([CH3:13])=O)[C:8]([CH3:14])=[CH:7][C:6]=1[OH:15].[Br:16][CH:17](Br)[CH3:18]>O.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Br:16][CH2:17][CH2:18][O:15][C:6]1[CH:7]=[C:8]([CH3:14])[C:9]([S:11][CH3:13])=[CH:10][C:5]=1[O:4][CH3:3]

Participants

6

Reactant 3

HCID 112011,1-DibromoethaneHCID 14798Sodium HydroxideHCID 12811402HCID 12811402, compound

Product 1

HCID 20484457HCID 20484457, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent2×

Procedure

A solution of sodium hydroxide (21 g) in water (75 ml) was added to 2-methoxy-5-methyl-4-methylsulphinylphenol (21 g), dibromoethane (160 ml) and benzyltriethylammonium chloride (1.26 g) and the resultant mixture heated at 60° for 18 hours. After cooling, water (50 ml) was added. The organic layer was separated, the aqueous layer extracted with dibromoethane (2×10 ml). The combined organic extracts were washed with 2 N aqueous sodium hydroxide solution (100 ml) and water (100 ml) and the solvent was evaporated under reduced pressure to give an orange oil, which on trituration with 40°-60° petroleum ether afforded a solid, which was filtered off, washed with further petroleum ether and dried in vacuo. The crude mono-ether (29.24 g), m.p. 66°-67° was used without further purification in the next stage. (A sample purified by column chromatography on Florisil eluting with dichloromethane followed by crystallisation from diethyl ether/40°-60° petroleum ether (1:3 v/v) had m.p. 72°-73°).

Workup

  1. temperatureAfter cooling
  2. customThe organic layer was separated
  3. extractionthe aqueous layer extracted with dibromoethane (2×10 ml)
  4. washThe combined organic extracts were washed with 2 N aqueous sodium hydroxide solution (100 ml) and water (100 ml)
  5. customthe solvent was evaporated under reduced pressure
  6. customto give an orange oil, which on trituration with 40°-60° petroleum ether
  7. customafforded a solid, which
  8. filtrationwas filtered off
  9. washwashed with further petroleum ether
  10. customdried in vacuo
  11. customThe crude mono-ether (29.24 g), m.p. 66°-67° was used without further purification in the next stage
  12. custom(A sample purified by column chromatography on Florisil eluting with dichloromethane
  13. customfollowed by crystallisation from diethyl ether/40°-60° petroleum ether (1:3 v/v)

Sources & evidence

ORD record
ord-da39a256220b41a2b4ac3536df14f069
Source dataset
uspto-grants-1983_10
Patent number
US04410548

Reaction notes

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