Sodium hydride → HCID 18699201, compound

HRID 2290146Notes

Reaction equation

HRID 2290146 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:9]([CH3:10])=[CH:8][C:7]([OH:11])=[C:6]([C:12]([CH3:16])([CH3:15])[CH2:13]Cl)[CH:5]=1>O1CCCC1>[Br:3][C:4]1[C:9]([CH3:10])=[CH:8][C:7]2[O:11][CH2:13][C:12]([CH3:16])([CH3:15])[C:6]=2[CH:5]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 186991894-Bromo-2-(2-chloro-1,1-dimethyl-ethyl)-5-methyl-phenol2×

Product 1

HCID 18699201HCID 18699201, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred, cooled (ice bath) suspension of sodium hydride (60% dispersion in mineral oil, 1.23 g, 30.85 mmol) in 50 mL of anhydrous tetrahydrofuran under argon, a solution of 4-bromo-2-(2-chloro-1,1-dimethyl-ethyl)-5-methyl-phenol (Compound 46, 6.2 g, 25.7 mmol) in 10 mL of anhydrous tetrahydrofuran was added. After 0.5 hour, the excess sodium hydride was quenched with methanol and the reaction mixture was evaporated in vacuo. The residue was diluted with water, extracted with ether and the organic phase was washed with brine. The organic extract was dried over anhydrous sodium sulfate, filtered and evaporated to an oil. Flash column chromatography of the oil over silica gel using hexanes as the eluent afforded the title compound as a clear oil (5.25 g, quantitative). 1H NMR (300 MHz, CDCl3): δ 7.23 (s, 1H), 6.70 (s, 1H), 4.24 (s, 2H), 2.35 (s, 3H), 1.33 (s, 6H).

Workup

  1. temperatureTo a stirred, cooled
  2. customthe excess sodium hydride was quenched with methanol
  3. customthe reaction mixture was evaporated in vacuo
  4. additionThe residue was diluted with water
  5. extractionextracted with ether
  6. washthe organic phase was washed with brine
  7. extractionThe organic extract
  8. dry with materialwas dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customevaporated to an oil

Sources & evidence

ORD record
ord-03d65f1b9a9d4adb91bf11312eab7ac3
Source dataset
uspto-grants-2000_07
Patent number
US06093838

Reaction notes

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