2,6-Dibromopyridine → 1-(6-Bromopyridin-2-yl)cyclobutanol

HRID 2207351Notes

Reaction equation

HRID 2207351 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Br:13])[N:8]=1.[C:14]1(=[O:18])[CH2:17][CH2:16][CH2:15]1.[NH4+].[Cl-]>ClCCl>[Br:13][C:9]1[N:8]=[C:7]([C:14]2([OH:18])[CH2:17][CH2:16][CH2:15]2)[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 122742,6-DibromopyridineHCID 14496CyclobutanoneHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 589324181-(6-Bromopyridin-2-yl)cyclobutanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

n-Butyllithium (6.85 mL, 11.0 mmol) was added to a suspension of 2,6-dibromopyridine (2.36 g, 9.96 mmol) in dichloromethane (60 mL) at −78° C. The reaction mixture was stirred for 15 minutes and cyclobutanone (0.838 g, 12.0 mmol) was added in one portion at −78° C. The reaction was stirred for an additional 30 minutes before pouring the reaction into a mixture of saturated aqueous NH4Cl and dichloromethane. The organic layer was concentrated to dryness and was purified by flash chromatography to yield 1-(6-bromopyridin-2-yl)cyclobutanol as a light yellow oil. MS ESI calc'd. for C9H11BrNO [M+H]+ 228 and 230. found 228 and 230.

Workup

  1. stirringThe reaction was stirred for an additional 30 minutes
  2. additionbefore pouring
  3. customthe reaction
  4. concentrationThe organic layer was concentrated to dryness
  5. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-ac477032319749d6a36faee92c631728
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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