Methyl iodide → HCID 86638343, compound

HRID 1694597Notes

Reaction equation

HRID 1694597 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:11]2([CH3:14])[CH2:13][CH2:12]2)[C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[C:15]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:11]2([CH3:14])[CH2:12][CH2:13]2)[C:5]([O:10][CH3:15])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86638342HCID 86638342, compound

Product 1

HCID 86638343HCID 86638343, compoundYield 102.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

step 3—To a solution of 74a (0.44 g, 1.7 mmol) in DMF (4 mL) was added K2CO3 (0.60 g, 4.4 mmol) and iodomethane (0.32 g, 2.3 mmol). The resulting mixture was stirred at 60° C. for 2 h. The reaction mixture was cooled to RT and partitioned between water and Et2O. The organic layer was washed sequentially with water and brine, dried (Na2SO4), filtered and concentrated to afford 0.47 g (96%) of 5-bromo-2-methoxy-3-(1-methylcyclopropyl)benzaldehyde (74b) as a light yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. custompartitioned between water and Et2O
  3. washThe organic layer was washed sequentially with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5d377bdfa98e43a0b3a514c96484835e
Source dataset
uspto-grants-2012_04
Patent number
US08158803B2

Reaction notes

Loading…