Potassium Carbonate → HCID 59314245, compound

HRID 1047834Notes

Reaction equation

HRID 1047834 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([CH3:11])[C:5]=1[OH:12].C([O-])([O-])=O.[K+].[K+].Br[CH:21]1[CH2:24][CH2:23][CH2:22]1>CN(C)C=O>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([CH3:11])[C:5]=1[O:12][CH:21]1[CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 78110BromocyclobutaneHCID 20074462Methyl 5-chloro-2-hydroxy-3-methylbenzoate

Product 1

HCID 59314245HCID 59314245, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
37 °C

Procedure

A 100 mL round bottom flask is charged with 5-chloro-2-hydroxy-3-methyl-benzoic acid methyl ester (0.92 g, 4.59 mmol). Dry N,N-dimethylformamide (DMF, 15 mL) and a stirring bar are added. Stirring is initiated. After dissolution, K2SO4 (1.90 g, 13.76 mmol) and bromocyclobutane (0.65 mL, 6.88 mmol) are added. After 12 days, tlc analysis (silica, 25% EtOAc/heptanes) indicated a slight consumption of starting material and the appearance of a UV positive spot with a slightly higher Rf value. The reaction is fitted with a heating mantle and warmed to 37° C. After 3 more days, tlc analysis (silica, 25% EtOAc/heptanes) indicates a slight consumption of starting material and complete conversion to a UV positive spot with a slightly higher Rf value. The reaction mixture is filtered through a pad of Celite. The filtrate is diluted with EtOAc and (100 mL) and transferred to a separatory funnel. The EtOAc solution is washed with saturated NaHCO3 (2×25 mL) and brine (25 mL), dried over MgSO4, filtered and evaporated by pumping to constant weight to give 0.79 g of semi-solid material.

Workup

  1. additionare added
  2. customa slight consumption of starting material
  3. customThe reaction is fitted with a heating mantle and
  4. customa slight consumption of starting material and complete conversion to a UV positive spot with a slightly higher Rf value
  5. filtrationThe reaction mixture is filtered through a pad of Celite
  6. additionThe filtrate is diluted with EtOAc and (100 mL)
  7. customtransferred to a separatory funnel
  8. washThe EtOAc solution is washed with saturated NaHCO3 (2×25 mL) and brine (25 mL)
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-17df2b0f108e4a0f8c4be5c802d67470
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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