Cesium carbonate → HCID 69871067, compound

HRID 2229045Notes

Reaction equation

HRID 2229045 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([Br:16])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[C:24]([CH3:31])([CH3:30])[C:25]([O:27][CH2:28][CH3:29])=[O:26]>CN(C=O)C>[CH2:28]([O:27][C:25](=[O:26])[C:24]([O:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:10][C:11]=1[Br:16])([CH3:31])[CH3:30])[CH3:29]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 109788072-Bromo-4-(phenylmethoxy)phenol

Product 1

HCID 69871067HCID 69871067, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 4-benzyloxy-2-bromo-phenol (9.37 g, 33.6 mmol) and Cs2CO3 (21.9 g, 67.2 mmol) in DMF (80 mL) was treated with ethyl bromoisobutyrate (15 mL, 100 mmol) and heated at 55° C. for 18 h. The reaction mixture was cooled and partitioned between ethyl acetate (250 mL) and H2O (100 mL). The organic layer was washed with brine (75 mL), dried (Na2SO4), and concentrated. The crude product was purified by flash chromatography using CH2Cl2:hexanes (2:3 to 3:2) to give a pale yellow oil (4.58 g, 35%): 1H NMR (400 MHz, CDCl3) δ1.29 (t, 3H, J=7.1 Hz), 1.57 (s, 6H), 4.25 (q, 2H, J=7.1 Hz), 4.98 (s, 2H), 6.79 (dd, 1H, J=3.2, 9.1 Hz), 6.89 (d, 1H, J=8.8 Hz), 7.17 (d, 1H, J=3.4 Hz), 7.32-7.40 (m, 5H); MS (ES) m/e # [M+1].

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between ethyl acetate (250 mL) and H2O (100 mL)
  3. washThe organic layer was washed with brine (75 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-da7ae75940b74f889db07819b27798dd
Source dataset
uspto-grants-2002_07
Patent number
US06417212B1

Reaction notes

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