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

HRID 2060592Notes

Reaction equation

HRID 2060592 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:4][CH:3]=1.[CH3:11][Mg]Br.O>C(OCC)C>[Br:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])([CH3:11])[CH3:9])[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 112985782-Acetyl-6-bromopyridineHCID 178418573HCID 178418573, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 1-(6-bromopyridin-2-yl)ethanone (5 g, 25.0 mmol) in diethyl ether (77 ml) at 0° C. was treated with methyl magnesium bromide (8.33 ml, 25.0 mmol). After 3 hours, water was added to quench excess methyl magnesium bromide, and then concentrated aqueous hydrogen chloride solution was added until two layers were obtained. The layers were separated and the aqueous layer was extracted with diethyl ether (3×50 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated to yield the title compound. LRMS (APCI) calc'd for C8H11BrNO [M+H]+: 216, Found: 216.

Workup

  1. customto quench excess methyl magnesium bromide
  2. additionconcentrated aqueous hydrogen chloride solution was added until two layers
  3. customwere obtained
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with diethyl ether (3×50 mL)
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-fe45f7cff98f469b9d420c6dd3cc6d79
Source dataset
uspto-grants-2012_10
Patent number
US08278335B2

Reaction notes

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