Ethyl bromoacetate → HCID 54094066, compound

HRID 580955Notes

Reaction equation

HRID 580955 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH2:8]([C:11]1[CH:16]=[C:15]([Br:17])[CH:14]=[CH:13][C:12]=1[OH:18])[CH:9]=[CH2:10].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:8]([C:11]1[CH:16]=[C:15]([Br:17])[CH:14]=[CH:13][C:12]=1[O:18][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:9]=[CH2:10]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 2584682-ALLYL-4-BROMOPHENOL

Product 1

HCID 54094066HCID 54094066, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Ethyl bromoacetate (1.68 g) was added to a stirred suspension of 2-allyl-4-bromophenol (2.13 g) and potassium carbonate (1.50 g) in butan-2-one (15 ml). The mixture was heated at reflux for 16 hours. The reaction mixture was cooled to ambient temperature and filtered. Water (100 ml) was added to the filtrate and the aqueous phase was extracted with ethyl acetate (3×50 ml). The ethyl acetate extracts were combined, washed with brine (2×25 ml), dried (MgSO4) and evaporated to give a solid which crystallised from hexane to give ethyl 2-allyl-4-bromophenoxyacetate (2.10 g), mp 70.5° C.; microanalysis, found: C, 52.0; H, 5.10%; C13H15BrO3 requires: C, 52.2; H, 5.05%; NMR (CDCl3) 1.29 (3H, t), 3.42 (2H, d), 4.25 (2H, q), 4.58 (2H, s), 5.07-5.17 (2H, m), 5.88-6.18 (1H, m), 6.60 (1H, d) and 7.20-7.27 (2H, m); m/z 300 (M+H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 hours
  3. filtrationfiltered
  4. additionWater (100 ml) was added to the filtrate
  5. extractionthe aqueous phase was extracted with ethyl acetate (3×50 ml)
  6. washwashed with brine (2×25 ml)
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customto give a solid which
  10. customcrystallised from hexane

Sources & evidence

ORD record
ord-a6ec198392534efd95a6b4c0de2e5dda
Source dataset
uspto-grants-1999_07
Patent number
US05919793

Reaction notes

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