Methyl iodide → HCID 23023145, compound

HRID 1664624Notes

Reaction equation

HRID 1664624 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:10])[CH:3]=1.[Li+].[CH3:12]C([N-]C(C)C)C.CI>C1COCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH2:10][CH3:12])[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 1442674-Bromo-2-methylbenzonitrileHCID 2724682Lithium diisopropylamide

Product 1

HCID 23023145HCID 23023145, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromo-2-methylbenzonitrile (0.4 g, 2.0 mmol) in dry THF (10 mL) was slowly added LDA (1.3 mL, 1.8 M in THF) at −78° C. and stirred at this temperature for additional 30 min. Methyl iodide (0.15 mL, 2.4 mmol) was added) at −78° C. to the above dark purple solution and the mixture was warmed to room temperature over 3 h. The reaction was quenched with water, extracted with ether, which was then was washed with brine, dried and concentrated. 4-Bromo-2-ethylbenzonitrile (0.34 g) was purified by Combiflash.

Workup

  1. customat −78° C.
  2. customThe reaction was quenched with water
  3. extractionextracted with ether, which
  4. washwas then was washed with brine
  5. customdried
  6. concentrationconcentrated
  7. custom4-Bromo-2-ethylbenzonitrile (0.34 g) was purified by Combiflash

Sources & evidence

ORD record
ord-af6d105605f04bc784a09c71fe3a70c3
Source dataset
uspto-grants-2011_10
Patent number
US08039471B2

Reaction notes

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