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

HRID 526047Notes

Reaction equation

HRID 526047 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 2N 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. 1H-NMR (400 MHz, CDCl3) δ: 7.56 (1H, t, J=7.8 Hz), 7.38 (1H, dd, J=7.8, 1.0 Hz), 7.36 (1H, dd, J=7.8, 1.0 Hz), 1.55 (6H, s). ESI-MS Found: m/z [M+H]+ 216, 218.

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-b9e84a69f2af460b8550baf792e62b83
Source dataset
uspto-grants-2016_05
Patent number
US09345705B2

Reaction notes

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