1-Bromopropane → HCID 22456881, compound

HRID 2186523Notes

Reaction equation

HRID 2186523 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([I:18])[C:16]=1[OH:17])[CH:12]=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][CH2:27][CH3:28]>CN(C=O)C.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([I:18])[C:16]=1[O:17][CH2:26][CH2:27][CH3:28])[CH:12]=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 22456878HCID 22456878, compound

Product 1

HCID 22456881HCID 22456881, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
77.5 °C

Procedure

To a mixture of 3-benzyloxy-4-hydroxy-5-iodo benzaldehyde (23.1 g, 0.065 mol) and potassium carbonate (11.70 g, 0.084 mol) in DMF (55 ml) was added 1-bromo propane (12.03 g, 0.09 mol). The reaction mixture was stirred at 75-80° C. for 12 h. The reaction mixture was cooled to room temperature, diluted with water and extracted with ether (480 ml). The ether layer was dried Na2SO4), filtered and concentrated. The crude product was purified on silica gel column using (1:18) EtOAc: light petroleum as eluent to give the 3-benzyloxy-4-propoxy-5-Iodo benzaldehyde (21.4 g, 83%). TLC: Ethyl acetate:light petroleum (1:9), Rf=0.5; 1H NMR (CDCl3, 200 MHz): δ 1.03 (t, J=7.21 Hz, 3H), 1.75 (m, 2H), 4.05 (t, J=6.66 Hz, 2H), 5.15 (s, 2H), 7.3-7.45 (m, 6H), 7.83 (d, J=1.54 Hz, 1H), 9.79 (s, 1H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ether (480 ml)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified on silica gel column

Sources & evidence

ORD record
ord-40cfcd6992df4f0b8a6a96b58736cc36
Source dataset
uspto-grants-2002_06
Patent number
US06403814B1

Reaction notes

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