Dimethylformamide → HCID 11160771, compound

HRID 1989824Notes

Reaction equation

HRID 1989824 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([CH3:12])([CH3:11])[CH:9]=[CH2:10])[C:5]([Cl:13])=[CH:4][C:3]=1[O:14][CH3:15].[Li]CCCC.CN([CH:24]=[O:25])C>C1COCC1>[Cl:13][C:5]1[C:6]([C:8]([CH3:12])([CH3:11])[CH:9]=[CH2:10])=[CH:7][C:2]([CH:24]=[O:25])=[C:3]([O:14][CH3:15])[CH:4]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11243225HCID 11243225, compoundHCID 178418339Butyllithium

Product 1

HCID 11160771HCID 11160771, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 1-bromo-4-chloro-5-(1,1-dimethyl-allyl)-2-methoxy-benzene (3.92 g, 0.0135 mol) in dry THF (30 mL) was cooled to −78° C. under argon. n-BuLi (2.5M, 6 mL, 0.0145 mol) was added keeping the temperature below −70° C. The yellow mixture was stirred for another 15 min and quenched with dry DMF (1.2 mL, 0.015 mol). The cooling bath was removed and the mixture was allowed to warm to 25° C. A saturated solution of NaHCO3 (30 mL) was added and then extracted with EtOAc (3×50 mL). The organic phase was dried (Na2SO4) and evaporated to dryness. The crude product was recrystallized from MeOH. Yield: 3.00 g (93%). GCMS: >99%

Workup

  1. customthe temperature below −70° C
  2. customThe cooling bath was removed
  3. additionA saturated solution of NaHCO3 (30 mL) was added
  4. extractionextracted with EtOAc (3×50 mL)
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. customevaporated to dryness
  7. customThe crude product was recrystallized from MeOH

Sources & evidence

ORD record
ord-b5383ab2cb924cd3ad62d7ff1e945467
Source dataset
uspto-grants-2010_01
Patent number
US07642367B2

Reaction notes

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