Sodium → HCID 13036752, compound

HRID 1719558Notes

Reaction equation

HRID 1719558 reaction equation
[Na].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[C:5]([C:10](=[O:15])[C:11](Br)([CH3:13])[CH3:12])[CH:4]=1>C(O)C.C1C=CC=CC=1>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]2[O:9][C:11]([CH3:13])([CH3:12])[C:10](=[O:15])[C:5]=2[CH:4]=1

Participants

5

Reactant 2

HCID 5360545SodiumHCID 14257623HCID 14257623, compound

Product 1

HCID 13036752HCID 13036752, compoundYield 82.5%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

With stirring under ice-cooling, 3 g of metallic sodium were added in 100 ml of absolute ethanol to dissolve the metal. Then, 12.5 g (0.045 mol) of 4-chloro-2-(2-bromoisobutyryl)phenol dissolved in 60 ml of benzene was added to the said solution dropwise for about 15 minutes under heating to reflux (internal temperature: 80° C.). After the completion of the dropping, the stirring was continued for additional 30-60 minutes with heating and the solution was vacuum-concentrated to one third in volume. The solution concentrated was diluted with large amount of water, and the solution was extracted with ether. The ether layer was washed with water, then vacuum-concentrated to dryness to produce 10 g of crude crystallized subject compound, 5-chloro-2,2-dimethyl-4-benzofuran. Then, the crude product was recrystallized from methanol, to obtain 7.3 g (yield: 82.5%) of the subject compound in colorless pillow crystal.

Workup

  1. temperaturecooling
  2. dissolutionto dissolve the metal
  3. additionwas added to the said solution dropwise for about 15 minutes
  4. temperatureunder heating
  5. temperaturewith heating
  6. concentrationthe solution was vacuum-concentrated to one third in volume
  7. concentrationThe solution concentrated
  8. additionwas diluted with large amount of water
  9. extractionthe solution was extracted with ether
  10. washThe ether layer was washed with water
  11. concentrationvacuum-concentrated to dryness
  12. customto produce 10 g of crude
  13. customcrystallized
  14. customThen, the crude product was recrystallized from methanol

Sources & evidence

ORD record
ord-66fd8044976c4a448f8fc53d4a169393
Source dataset
uspto-grants-1985_09
Patent number
US04540704

Reaction notes

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