Hydrochloric Acid → 2-(6-Bromopyridin-2-yl)propan-2-ol

HRID 1630381Notes

Reaction equation

HRID 1630381 reaction equation
C[Mg]I.C([O:6][CH2:7][CH3:8])C.[CH2:9](OCC)C.[Br:14][C:15]1[N:20]=[C:19](C(OC)=O)[CH:18]=[CH:17][CH:16]=1.Cl>O>[Br:14][C:15]1[N:20]=[C:19]([C:7]([OH:6])([CH3:8])[CH3:9])[CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 16217886Methyl 6-bromopyridine-2-carboxylateHCID 178467823HCID 178467823, compound

Product 1

HCID 227143012-(6-Bromopyridin-2-yl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a nitrogen atmosphere, 30 mL of 3 M methylmagnesium iodide/diethyl ether was added to 300 mL of diethyl ether solution of 8.72 g of methyl 6-bromopyridine-2-carboxylate. Water and 2 N hydrochloric acid were added to the reaction liquid, and extracted with ethyl acetate. This was washed with aqueous saturated sodium hydrogencarbonate solution and saturated saline water, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure to obtain 8.51 g of crude 2-(6-bromo-2-pyridinyl)-2-propanol as a yellow oily substance.

Workup

  1. extractionextracted with ethyl acetate
  2. washThis was washed with aqueous saturated sodium hydrogencarbonate solution and saturated saline water
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customThe solvent was evaporated away under reduced pressure

Sources & evidence

ORD record
ord-fccfef4e1dfe4ee4826906e0de53ba7b
Source dataset
uspto-grants-2014_07
Patent number
US08791125B2

Reaction notes

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