Sodium hydride → 5-Bromo-3,3-dimethyl-2,3-dihydro-1-benzofuran

HRID 2085568Notes

Reaction equation

HRID 2085568 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]([CH3:15])([CH3:14])[CH2:12]Cl)[CH:5]=1>O1CCCC1>[Br:3][C:4]1[CH:9]=[CH:8][C:7]2[O:10][CH2:12][C:11]([CH3:15])([CH3:14])[C:6]=2[CH:5]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 22731307HCID 22731307, compound2×

Product 1

HCID 53235955-Bromo-3,3-dimethyl-2,3-dihydro-1-benzofuranYield 75.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred, cooled (ice bath) suspension of sodium hydride (60% dispersion in mineral oil, 0.024 g, 0.6 mmol) in 10 mL of anhydrous tetrahydrofuran under argon, a solution of 4-bromo-2-(2-chloro-1,1-dimethyl-ethyl)phenol (Intermediate 1, 0.13 g, 0.5 mmol) in 2 mL of anhydrous tetrahydrofuran was added. After 0.5 h, 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 (230-400 mesh) using 2.5% ethyl acetate in hexane as the eluent afforded the title compound as a pale yellow oil (0.085 g, 75.7%).

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-98171a0a718142dea3fe5556f70abe07
Source dataset
uspto-grants-2004_04
Patent number
US06720423B2

Reaction notes

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