Dimethylformamide → HCID 59473813, compound

HRID 2069710Notes

Reaction equation

HRID 2069710 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:3]=1.C([Mg]Cl)(C)C.[Li]CCCC.CN([CH:26]=[O:27])C>C1COCC1>[C:9]([C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([F:8])[CH:5]=1)[CH:26]=[O:27])([CH3:12])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 534356461-Bromo-3-(1,1-dimethylethyl)-5-fluorobenzeneHCID 178418339ButyllithiumHCID 178418918HCID 178418918, compound

Product 1

HCID 59473813HCID 59473813, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Bromo-3-tert-butyl-5-fluorobenzene (323.2 g, 1.4 moles) was dissolved in THF (3.3 L) and cooled −10° C. iPrMgCl (2M solution in THF, 0.5 eq, 350 mL) was added over 20 min, followed by nBuLi (2.5M solution in hexanes, 1.0 eq, 560 mL) over two hours. DMF (4 eq, 450 mL) was added over one hour then stirred for 45 minutes and quenched with 3M HCl (1000 mL). The layers were separated and the aqueous fraction was diluted with water (1 L) and extracted with ethyl acetate (1 L). The organic fractions were combined and washed with water (2×2 L). The organic fraction was concentrated to provide an orange oil (252 g, quant), used directly in the next reaction.

Workup

  1. additionwas added over 20 min
  2. customquenched with 3M HCl (1000 mL)
  3. customThe layers were separated
  4. additionthe aqueous fraction was diluted with water (1 L)
  5. extractionextracted with ethyl acetate (1 L)
  6. washwashed with water (2×2 L)
  7. concentrationThe organic fraction was concentrated
  8. customto provide an orange oil (252 g, quant)
  9. customused directly in the next reaction

Sources & evidence

ORD record
ord-b8b1a3ebcbb44452a4a8d1b2f4175eb6
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

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