Ethyl bromoacetate → HCID 17956300, compound

HRID 1351029Notes

Reaction equation

HRID 1351029 reaction equation
[F:1][C:2]([F:24])([F:23])[CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][OH:22].CC(C)([O-])C.[K+].Br[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34]>C1(C)C=CC=CC=1>[F:1][C:2]([F:23])([F:24])[CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 17956301HCID 17956301, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 17956300HCID 17956300, compoundYield 21.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of the product of step (d) (1.5 g) in toluene (30 mL) was added potassium tert-butoxide (0.69 g) and the resulting mixture was stirred at room temperature for 3 hours. Ethyl bromoacetate (1.38 g) was added and the reaction was stirred at 130° C. for 48 hours. The solvent was removed in vacuo and the residue was dissolved in dichloromethane (500 mL) and washed with water (2×400 mL). The organic layer was washed with brine (300 mL), dried and the solvent was removed in vacuo. The residue was purified by column chromatography on silica gel (Biotage), eluting with 65–75% ethyl acetate in cyclohexane to give the title compound as a brown oil (0.40 g). LC retention time 2.77 min. Mass spectrum m/z 468 [MNH4+]

Workup

  1. stirringthe reaction was stirred at 130° C. for 48 hours
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in dichloromethane (500 mL)
  4. washwashed with water (2×400 mL)
  5. washThe organic layer was washed with brine (300 mL)
  6. customdried
  7. customthe solvent was removed in vacuo
  8. customThe residue was purified by column chromatography on silica gel (Biotage)
  9. washeluting with 65–75% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-4a7f479fb550434b8480c1879fe3fb71
Source dataset
uspto-grants-2007_05
Patent number
US07217409B2

Reaction notes

Loading…