Benzyl Bromide → HCID 58764225, compound

HRID 859614Notes

Reaction equation

HRID 859614 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:15]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH3:26])=[CH:19][C:18]=1[OH:27])[CH3:16]>CN(C=O)C>[CH2:7]([O:27][C:18]1[CH:19]=[C:20]([O:23][CH2:24][CH2:25][CH3:26])[CH:21]=[CH:22][C:17]=1[CH2:15][CH3:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 58764219HCID 58764219, compound

Product 1

HCID 58764225HCID 58764225, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

Potassium carbonate (17.8 g, 0.13 mol) followed by benzyl bromide (5.12 mL, 42.9 mmol) were added to a solution of 2-ethyl-5-propoxy-phenol (7.74 g, 42.9 mmol) in DMF (60 mL). The mixture was stirred at 45° C. for 15 hours and then partitioned between H2O and EtOAc. The organic layer was washed with 1 N HCl, brine, dried over Na2SO4 and concentrated to a brown oil. Purification by flash column chromatography (0% to 20% EtOAc in hexanes) gave the product as a clear oil (6.1 g, 55%). 1H NMR (400 MHz, CDCl3): δ 1.02 (t, J=7.6 Hz, 3 H), 1.19 (t, J=7.6 Hz, 3 H), 1.78 (q, J=7.6 Hz, 2 H), 2.63 (q, J=7.6 Hz, 2 H), 3.88 (t, J=6.6 Hz, 2 H), 5.05 (s, 2 H), 6.44 (dd, J8.1, 2.3 Hz, 1 H), 6.51 (dd, J=2.3 Hz, 1 H), 7.05 (d, J=8.3 Hz, 1 H), 7.31 (m, 1 H), 7.38 (m, 2 H), 7.44 (m, 2 H).

Workup

  1. custompartitioned between H2O and EtOAc
  2. washThe organic layer was washed with 1 N HCl, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to a brown oil
  5. customPurification by flash column chromatography (0% to 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-476a7b828610448a82841f3d05310866
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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