2-Bromopropane → 3,5-difluoro-4-isopropoxybenzaldehyde

HRID 2235386Notes

Reaction equation

HRID 2235386 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:11])[C:9]=1[OH:10])[CH:5]=[O:6].C([O-])([O-])=O.[K+].[K+].Br[CH:19]([CH3:21])[CH3:20]>CC#N>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:11])[C:9]=1[O:10][CH:19]([CH3:21])[CH3:20])[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 101925843,5-Difluoro-4-hydroxybenzaldehyde

Product 1

HCID 791111833,5-difluoro-4-isopropoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

To a suspension of 3,5-difluoro-4-hydroxy-benzaldehyde as a colourless solid (0.81 g) and K2CO3 (2.14 g; 15.4 mmol) in MeCN (15 ml) is added 2-bromopropane (1.45 ml) dropwise. The mixture is stirred at 65° C. for 24 h. After evaporation of the solvent the residue is taken-up in Et2O and water. The organic layer is separated and extracted with brine, dried over MgSO4 and evaporated to give 3,5-difluoro-4-isopropoxy-benzaldehyde (0.14 g).

Workup

  1. customAfter evaporation of the solvent the residue
  2. customThe organic layer is separated
  3. extractionextracted with brine
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-25e568033b0a40ef8924fd7400f68b54
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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