Dimethyl Carbonate → Methyl 2-(4-bromopyridin-2-yl)acetate

HRID 572934

Reaction equation

HRID 572934 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[CH:3]=1.[Li+].CC([N-]C(C)C)C.[C:17](=O)([O:20]C)[O:18][CH3:19]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][C:17]([O:18][CH3:19])=[O:20])[CH:3]=1

Participants

5

Reactant 3

HCID 12021Dimethyl CarbonateHCID 2724682Lithium diisopropylamideHCID 27628354-Bromo-2-methylpyridine

Product 1

HCID 84071108Methyl 2-(4-bromopyridin-2-yl)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-bromo-2-methylpyridine (1 g, 5.8 mmol) in 15 mL of anhydrous THF was added LDA (9.2 mL, 2M) dropwise at −70, stirred for 30 min dimethyl carbonate (630 mg, 7.0 mmol) was added dropwise to the above solution. After stirring for another 1 h, LC-MS found the reaction finished. It was quenched by Sat. NH4Cl solution and extracted with EtOAc. The organic layer was separated and evaporated under reduced pressure. The crude product was purified by a standard method to give desired product. LC-MS: m/z (M+H) 231.1.

Workup

  1. additionwas added dropwise to the above solution
  2. customIt was quenched by Sat. NH4Cl solution
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. customevaporated under reduced pressure
  6. customThe crude product was purified by a standard method

Sources & evidence

ORD record
ord-a47a24c68cc7420984d4030bc5703904
Source dataset
uspto-grants-2015_05
Patent number
US09029531B2

Linked notes

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