Hydrogen Bromide → HCID 59186000, compound

HRID 1671329Notes

Reaction equation

HRID 1671329 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[C:4]([CH3:12])[CH:3]=1.[BrH:13].BrBr.C([O-])([O-])=O.[Na+].[Na+]>>[Br:13][CH:9]([CH3:10])[C:8]([C:5]1[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][C:4]=1[CH3:12])=[O:11]

Participants

5

Reactant 4

HCID 260Hydrogen BromideHCID 10340Sodium CarbonateHCID 24408Bromine2×HCID 86638940HCID 86638940, compound

Product 1

HCID 59186000HCID 59186000, compound

Procedure

1-(6-Chloro-4-methyl-pyridin-3-yl)-propan-1-one (100 mg, 0.545 mmol) is dissolved in hydrobromic acid (48%) (2 ml, 17.68 mmol); to this is then added bromine (0.031 ml, 0.599 mmol) dropwise and the resulting orange solution stirred at RT. After 4 hours, further 0.2 eq (5 ul) of bromine is added and the reaction is left stirring O/N at RT. The reaction mixture is basified by careful addition of 2M Na2CO3 (5 ml) and then extracted into EtOAc (2×25 ml). The combined organic phase is washed with H2O, brine, dried (MgSO4) and evaporated to give a clear oil. The crude material is chromatographed on silica gel (20 g) eluting with (10% EtOAc/iso-hexane) to give the desired compound; MS: m/z 262.1 [M+H]+; 1H NMR (400 MHz, (CDCl3) δ 7.9 (d, 1H), 7.3 (d, 1H), 5.1 (q, 1H), 2.7 (s, 3H), 1.9 (d, 3H).

Workup

  1. waitthe reaction is left
  2. extractionextracted into EtOAc (2×25 ml)
  3. washThe combined organic phase is washed with H2O, brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give a clear oil
  7. customThe crude material is chromatographed on silica gel (20 g)
  8. washeluting with (10% EtOAc/iso-hexane)

Sources & evidence

ORD record
ord-1c3d487a3ec44abe8fd9f1663b927b8c
Source dataset
uspto-grants-2011_08
Patent number
US07994203B2

Reaction notes

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