Cesium carbonate → 3-((3-Bromophenoxy)methyl)pentan-3-ol

HRID 882405Notes

Reaction equation

HRID 882405 reaction equation
[CH2:1]([C:3]1([CH2:6][CH3:7])[CH2:5][O:4]1)[CH3:2].[Br:8][C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[Br:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=1)[O:15][CH2:5][C:3]([OH:4])([CH2:6][CH3:7])[CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 115633-BromophenolHCID 2959712,2-Diethyloxirane

Product 1

HCID 673170023-((3-Bromophenoxy)methyl)pentan-3-ol

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

2,2-Diethyloxirane (6.5 g of a 60% crude, 40 mmol), 3-bromophenol (5.7 g, 33 mmol), and cesium carbonate (12.0 g, 37 mmol) were combined in anhydrous DMSO (20 mL) in a sealed pressure tube and the reaction was stirred and heated at 120° C. for 2 d. Crude product was extracted from water with diethyl ether. The combined organic was washed with brine, dried over Na2SO4, filtered and concentrated under reduced vacuum. Purification by flash chromatography (0-20% EtOAc/hexanes gradient) gave 3-((3-bromophenoxy)methyl)pentan-3-ol as a colorless oil. Yield (7.1 g, 79%): NMR (400 MHz, CDCl3) δ 7.19 (t, J=8.0 Hz, 1H), 7.05-7.12 (m, 2H), 6.90-6.94 (m, 1H), 4.31 (s, 1H), 3.71 (s, 2H), 1.41-1.55 (m, 4H), 0.80 (t, J=7.6 Hz, 6H).

Workup

  1. extractionCrude product was extracted from water with diethyl ether
  2. washThe combined organic was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced vacuum
  6. customPurification by flash chromatography (0-20% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-c6c240512c074880aca8e4a65ae6d838
Source dataset
uspto-grants-2015_03
Patent number
US08993807B2

Reaction notes

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