Water → 3-Bromo-5-tert-butyl-6-isopropoxy-2-methyl-benzaldehyde

HRID 2377469Notes

Reaction equation

HRID 2377469 reaction equation
[Br:1][C:2]1[C:3]([CH3:15])=[C:4]([C:7]([OH:14])=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:9]=1)[CH:5]=[O:6].[H-].[Na+].I[CH:19]([CH3:21])[CH3:20].O>CN(C)C=O>[Br:1][C:2]1[C:3]([CH3:15])=[C:4]([C:7]([O:14][CH:19]([CH3:21])[CH3:20])=[C:8]([C:10]([CH3:11])([CH3:12])[CH3:13])[CH:9]=1)[CH:5]=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 211071503-Bromo-5-tert-butyl-6-hydroxy-2-methyl-benzaldehyde2×

Product 1

HCID 211071513-Bromo-5-tert-butyl-6-isopropoxy-2-methyl-benzaldehydeYield 64.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A stirred, cooled (ice bath) solution of 3-bromo-5-tert-butyl-6-hydroxy-2-methyl-benzaldehyde (Intermediate 140, 0.58 g, 2.14 mmol) in anhydrous N,N-dimethylformamide (10 mL) was treated with sodium hydride (0.34 g of 60% suspension in mineral oil, 8.56 mmol). After 30 minutes, 2-iodopropane (1.3 mL, 12.84 mmol) was added and the reaction mixture was heated at 75° C. overnight. The reaction mixture was then cooled and poured into iced water and extracted with diethyl ether. The organic extract was then washed with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to an oil. Flash column chromatography using 2-4% ethyl acetate in hexane as the eluent afforded the title product (0.43 g, 64%).

Workup

  1. temperatureThe reaction mixture was then cooled
  2. extractionextracted with diethyl ether
  3. extractionThe organic extract
  4. washwas then washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo to an oil

Sources & evidence

ORD record
ord-384f6cee820c4964b1299dbd21984ec7
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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