4-Bromo-2,6-diisopropylaniline → HCID 58526155, compound

HRID 1922328Notes

Reaction equation

HRID 1922328 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([CH:9]([CH3:11])[CH3:10])[C:5]([NH2:6])=[C:4]([CH:12]([CH3:14])[CH3:13])[CH:3]=1.[Li]CCCC.Cl[Si:21]([CH:24]1[C:28]2[S:29][CH:30]=[CH:31][C:27]=2[C:26]([CH3:32])=[C:25]1[CH3:33])([CH3:23])[CH3:22]>C1COCC1>[Br:1][C:2]1[CH:8]=[C:7]([CH:9]([CH3:10])[CH3:11])[C:5]([NH:6][Si:21]([CH:24]2[C:28]3[S:29][CH:30]=[CH:31][C:27]=3[C:26]([CH3:32])=[C:25]2[CH3:33])([CH3:22])[CH3:23])=[C:4]([CH:12]([CH3:14])[CH3:13])[CH:3]=1

Participants

5

Reactant 3

HCID 117801144-Bromo-2,6-diisopropylanilineHCID 58526148Chloro(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl)dimethylsilaneHCID 178418339Butyllithium

Product 1

HCID 58526155HCID 58526155, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under an argon atmosphere, to a solution of 18.9 g (73.8 mmol) of 4-bromo-2,6-diisopropylaniline in 200 ml of THF, 29.5 ml of 2.5 M (73.8 mmol) nBuLi in hexanes was added at −80° C. This mixture was warmed for ca. 1 hour to ambient temperature. Then, the resulting solution was added dropwise over ca. 1 hour, while vigorously stirring, to a solution of 17.9 g (73.8 mmol) of chloro(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl)dimethylsilane in 100 ml of THF. The resulting mixture was stirred overnight at ambient temperature, and then, evaporated to dryness. To the residue, 150 ml of toluene was added. This mixture was filtered through a glass frit (G4). The filtrate was evaporated to dryness. Fractional distillation gave a yellow liquid, bp 180° C./0.1 mm Hg. The product crystallizes slowly at ambient temperature. Yield 11.9 g (35%).

Workup

  1. temperatureThis mixture was warmed for ca. 1 hour to ambient temperature
  2. additionThen, the resulting solution was added dropwise over ca. 1 hour
  3. customevaporated to dryness
  4. additionTo the residue, 150 ml of toluene was added
  5. filtrationThis mixture was filtered through a glass frit (G4)
  6. customThe filtrate was evaporated to dryness
  7. distillationFractional distillation
  8. customgave a yellow liquid, bp 180° C./0.1 mm Hg
  9. customThe product crystallizes slowly at ambient temperature

Sources & evidence

ORD record
ord-4bcb3e5cc2a541c98d0859388db2b6fb
Source dataset
uspto-grants-2012_05
Patent number
US08173828B2

Reaction notes

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