Hydrochloric Acid → HCID 59539639, compound

HRID 1526763Notes

Reaction equation

HRID 1526763 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[C:4]([Br:12])[CH:3]=1.[Li]CCCC.CN([CH:21]=[O:22])C.Cl>CCOCC>[Br:12][C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=1)[CH:21]=[O:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228Dimethylformamide2×HCID 27611701,3-dibromo-5-tert-butylbenzeneHCID 178418339Butyllithium2×

Product 1

HCID 59539639HCID 59539639, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

1,3-Dibromo-5-tert-butylbenzene (50 g, 0.17 mol) was dissolved in anhydrous ether (200 mL) in a dried flask under nitrogen. The reaction mixture was cooled to −78° C. and stirred under nitrogen atmosphere. A 2.46 M solution of n-BuLi in hexanes (171.2 mL, 0.171 mol) was added dropwise to the above solution and the reaction mixture was stirred at −78° C. for 30 minute after complete addition of n-BuLi. After 30 minute of stirring at −78° C., the reaction mixture was warmed to −30° C. DMF (16 mL, 0.2 mol) was added to the above reaction mixture dropwise, keeping the reaction mixture below −20° C. After addition of DMF, the reaction mixture was warmed slowly to 0° C. (30 minute) and then stirring was continued overnight to obtain a yellow-orange solution. The reaction mixture was poured into 400 mL of chilled 10% aqueous HCl and the mixture was stirred for 15 minutes. The ether layer was separated, washed with water (2×250 mL), dried over anhydrous Na2SO4, filtered and evaporated in vacuo to give the product as a pale yellow viscous liquid. The crude product was dissolved in dichloromethane (250 mL) and passed through a small pad of silica gel (250 g). Evaporation of the solvent in vacuo gave the product as a pale yellow viscous liquid (41.2 g).

Workup

  1. stirringthe reaction mixture was stirred at −78° C. for 30 minute
  2. stirringAfter 30 minute of stirring at −78° C.
  3. temperaturethe reaction mixture was warmed to −30° C
  4. customthe reaction mixture below −20° C
  5. temperaturethe reaction mixture was warmed slowly to 0° C. (30 minute)
  6. stirringstirring
  7. customto obtain a yellow-orange solution
  8. stirringthe mixture was stirred for 15 minutes
  9. customThe ether layer was separated
  10. washwashed with water (2×250 mL)
  11. dry with materialdried over anhydrous Na2SO4
  12. filtrationfiltered
  13. customevaporated in vacuo

Sources & evidence

ORD record
ord-209836a70de74414b479f42f0ab24126
Source dataset
uspto-grants-2015_07
Patent number
US09085606B2

Reaction notes

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