Potassium Carbonate → HCID 18782514, compound

HRID 1420837Notes

Reaction equation

HRID 1420837 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].Br[CH:14]1[CH2:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH:14]1[CH2:17][CH2:16][CH2:15]1)[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 78110BromocyclobutaneHCID 4778958Methyl 3-bromo-4-hydroxybenzoate

Product 1

HCID 18782514HCID 18782514, compoundYield 40.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 3-bromo-4-hydroxybenzoate (Description 64, 2.3 g, 10 mmol), bromocyclobutane (2.0 g, 15 mmol) and potassium carbonate (2.42 g, 17.5 mmol) in DMF (25 ml) was stirred at room temperature for 3 days then at 70° C. for 6 h. The mixture was cooled, diluted with water (150 ml) and extracted with ethyl acetate (4×25 ml). The combined organic fractions were washed with aqueous sodium hydroxide (1M, 25 ml), dried (MgSO4), and the solvent was evaporated under reduced pressure to give the title compound as a gum (1.15 g). 1H NMR (CDCl3) δ 1.66-1.77 (1 H, m), 1.88-1.93 (1 H, m), 2.22-2.31 (2 H, m), 2.46-2.60 (2 H, m), 3.89 (3 H, s), 4.75 (1 H, app. pent, J 7.0 Hz), 6.74 (1 H, d, J 8.6 Hz), 7.91 (1 H, dd, J 8.6, 2.1 Hz), and 8.23 (1 H, d, J 2.1 Hz).

Workup

  1. waitat 70° C. for 6 h
  2. temperatureThe mixture was cooled
  3. extractionextracted with ethyl acetate (4×25 ml)
  4. washThe combined organic fractions were washed with aqueous sodium hydroxide (1M, 25 ml)
  5. dry with materialdried (MgSO4)
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b4b1e89f999848239b4fa1bb34972007
Source dataset
uspto-grants-2000_06
Patent number
US06071927

Reaction notes

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