Water → 2-(6-Bromopyridin-2-yl)propan-2-ol

HRID 2079753Notes

Reaction equation

HRID 2079753 reaction equation
Br[C:2]1C(Br)=C(NC([C@@H]2C[C@H]2C)=O)SN=1.[Br:15][C:16]1[N:21]=[C:20]([C:22](=[O:24])[CH3:23])[CH:19]=[CH:18][CH:17]=1.O>O1CCCC1.C(OCC)(=O)C>[Br:15][C:16]1[N:21]=[C:20]([C:22]([OH:24])([CH3:2])[CH3:23])[CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 962WaterHCID 112985782-Acetyl-6-bromopyridineHCID 67103560(R,R)-N-[3,4-dibromoisothiazol-5-yl]-2-methylcyclopropanecarboxamide

Product 1

HCID 227143012-(6-Bromopyridin-2-yl)propan-2-olYield 98%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Add a solution of methyl magnesium bromide (3.0; M, 9.7; mL, 29.09; mmol) in tetrahydrofuran dropwise over 20; min to a cooled solution of 1-(6-bromo-pyridin-2-yl)-ethanone (5; g, 24.25; mmol) in anhydrous tetrahydrofuran (48.5; mL) at 0° C. Upon completion of the reaction, add water (exothermic), dilute with ethyl acetate (50; mL) and separate the layers. Extract the aqueous layer once with ethyl acetate (50; mL). Dry the combined organic layers over sodium sulfate, filter and concentrate to give the title compound as a pale yellow liquid (5.69; g, 98%) that is used without further purification. 1H NMR (CDCl3) δ 1.55; (s, 6H), 4.07; (s, 1H), 6.59; (t, 1H), 7.37; (t, 2H), 7.55; (t, 1H).

Workup

  1. customat 0° C
  2. customUpon completion of the reaction
  3. customseparate the layers
  4. extractionExtract the aqueous layer once with ethyl acetate (50; mL)
  5. dry with materialDry the combined organic layers over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-b91aa2e35b1b4d6199702c0404f46b12
Source dataset
uspto-grants-2011_04
Patent number
US07932274B2

Reaction notes

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