Water → HCID 59314239, compound

HRID 1047893Notes

Reaction equation

HRID 1047893 reaction equation
Br[CH:2]1[CH2:5][CH2:4][CH2:3]1.[CH3:6][O:7][C:8](=[O:19])[C:9]1[CH:14]=[C:13]([CH:15]=[O:16])[CH:12]=[C:11]([CH3:17])[C:10]=1[OH:18].O>CN(C=O)C.[I-].[K+]>[CH3:6][O:7][C:8](=[O:19])[C:9]1[CH:14]=[C:13]([CH:15]=[O:16])[CH:12]=[C:11]([CH3:17])[C:10]=1[O:18][CH:2]1[CH2:5][CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 962WaterHCID 78110BromocyclobutaneHCID 593141335-Formyl-2-hydroxy-3-methyl-benzoic acid methyl ester

Product 1

HCID 59314239HCID 59314239, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of bromocyclobutane (1.39 g, 10.3 mmol), potassium iodide (43 mg, 5 mol %), and CsCO3 (3.84 g, 11.84 mmol) in DMF (18 mL) is added 5-formyl-2-hydroxy-3-methyl-benzoic acid methyl ester (1.0 g, 5.15 mmol). The reaction is placed in the microwave reactor and heated at 110° C. for 6 h. Water (50 mL) is added to the reaction and the solution is extracted with EtOAc (3×40 mL). The combined organic layers are dried over anhydrous MgSO4 and concentrated in vacuo to give product (282) as orange-yellow oil (1.20 g, 94%).

Workup

  1. extractionthe solution is extracted with EtOAc (3×40 mL)
  2. dry with materialThe combined organic layers are dried over anhydrous MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9cc3ee78b07a4632bd6ef9ab63ad897a
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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