Methyl iodide → HCID 11747664, compound

HRID 1924443Notes

Reaction equation

HRID 1924443 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].CI.[C:17]([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOCC.O>[Br:1][C:2]1[CH:3]=[C:4]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:5]([O:10][CH3:17])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 7970065-bromo-3-tert-butyl-2-hydroxybenzaldehyde

Product 1

HCID 11747664HCID 11747664, compoundYield 98.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 27 (3.83 g), MeI (2.32 mL) and K2CO3 (6.18 g) in DMF (50 mL) was heated at 50° C. for 1 h then cooled to RT and diluted with ether and water. The organic layer was thrice washed with water then brine, dried (MgSO4) and concentrated to afford 3.99 g of 5-bromo-3-tert-butyl-2-methoxybenzaldehyde (28) as a yellow solid.

Workup

  1. temperaturethen cooled to RT
  2. washThe organic layer was thrice washed with water
  3. dry with materialbrine, dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-25c2f4a1937845a79a35dd34d318352f
Source dataset
uspto-grants-2012_05
Patent number
US08178547B2

Reaction notes

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