Potassium Carbonate → Methyl 3-cyano-4-(cyclopropylmethoxy)benzoate

HRID 2192479Notes

Reaction equation

HRID 2192479 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[OH:13])[C:6]([O:8][CH3:9])=[O:7])#[N:2].Br[CH2:15][CH:16]1[CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH2:15][CH:16]1[CH2:18][CH2:17]1)[C:6]([O:8][CH3:9])=[O:7])#[N:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 11769089Methyl 3-cyano-4-hydroxybenzoate

Product 1

HCID 66877477Methyl 3-cyano-4-(cyclopropylmethoxy)benzoateYield 47.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 3-cyano-4-hydroxybenzoate (D22; 120 mg, 0.677 mmol), (bromomethyl)cyclopropane (Aldrich; 0.099 ml, 1.016 mmol), and potassium carbonate (140 mg, 1.016 mmol) in dry N,N-dimethylformamide (DMF) (2 ml) was heated under microwave irradiation at 150° for 90 mins. The cooled mixture was partitioned between water (30 ml) and ethyl acetate (3×25 ml), and the organic layer was washed with 50:50 brine:water and brine, dried (MgSO4) and evaporated in vacuo to give a light brown crystalline solid which was purified by flash chromatography on silica gel, eluting with 0-30% ethyl acetate-cyclohexane. The appropriate fractions were combined and evaporated in vacuo to give the title compound as a white solid (74 mg)

Workup

  1. temperaturewas heated under microwave irradiation at 150° for 90 mins
  2. customThe cooled mixture was partitioned between water (30 ml) and ethyl acetate (3×25 ml)
  3. washthe organic layer was washed with 50:50 brine
  4. dry with materialwater and brine, dried (MgSO4)
  5. customevaporated in vacuo
  6. customto give a light brown crystalline solid which
  7. customwas purified by flash chromatography on silica gel
  8. washeluting with 0-30% ethyl acetate-cyclohexane
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-f8ca440489c9496fbc86e4b5f4c237c3
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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