Methanol → Methyl 2-(5-broMopyridin-2-yl)acetate

HRID 1175628Notes

Reaction equation

HRID 1175628 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[N:7][CH:8]=1.OS(O)(=O)=O.[CH3:18]O>>[Br:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([O:12][CH3:18])=[O:11])=[N:7][CH:8]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 534036862-(5-Bromopyridin-2-yl)acetic acid hydrochloride

Product 1

HCID 53419526Methyl 2-(5-broMopyridin-2-yl)acetateYield 92%

Conditions

Temperature
80 °C

Procedure

2-(5-Bromopyridin-2-yl)acetic acid hydrochloride (example 42e) (2.34 g, 9.3 mmol) was dissolved in MeOH (18 mL) and conc. H2SO4 (1.5 mL). The mixture was stirred at 80° C. overnight. The solvent was removed under reduced pressure and the mixture was treated with sat. NaHCO3 then extracted with EtOAc, washed with brine, dried over MgSO4, filtered and evaporated to give methyl 2-(5-bromopyridin-2-yl)acetate as a yellow oil (1.97 g, 92%). 1H NMR (400 MHz, dMSO): δ 3.60 (s, 3H), 3.83 (s, 2H), 7.34-36 (d, 1H), 7.99-8.02 (dd, 1H), 8.60-8.61 (d, 1H); MS+H (230, 231).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe mixture was treated with sat. NaHCO3
  3. extractionthen extracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-cf799e2eeba0474c8db3fd5d53dc0f49
Source dataset
uspto-grants-2010_11
Patent number
US07842324B2

Reaction notes

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