2,6-Lutidine → HCID 21093748, compound

HRID 1349941Notes

Reaction equation

HRID 1349941 reaction equation
N1C(C)=CC=CC=1C.[Br:9][C:10]1[CH:11]=[C:12]([N+:20]([O-:22])=[O:21])[C:13]([O:18][CH3:19])=[C:14]([CH:17]=1)[CH2:15]O.[Br-:23].[Li+].CS(OS(C)(=O)=O)(=O)=O>O1CCCC1>[Br:9][C:10]1[CH:11]=[C:12]([N+:20]([O-:22])=[O:21])[C:13]([O:18][CH3:19])=[C:14]([CH:17]=1)[CH2:15][Br:23]

Participants

6

Reactant 4

HCID 79372,6-LutidineHCID 81560Methanesulfonic anhydrideHCID 82050Lithium BromideHCID 69353261HCID 69353261, compound

Product 1

HCID 21093748HCID 21093748, compoundYield 118.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2,6-Lutidine (10.5 mL) was added to a stirring solution of 5-bromo-2-methoxy-3-nitrobenzyl alcohol (13.6 g) and lithium bromide (11.75 g) in anhydrous tetrahydrofuran (200 mL) at 0° C. A solution of methanesulfonic anhydride (11.8 g) in anhydrous tetrahydrofuran (20 mL) was added dropwise. The resulting mixture was left to stir at room temperature for 16 h. It was partitioned between diethyl ether (250 mL) and saturated sodium hydrogen carbonate (150 mL). The organic layer was dried (sodium sulfate) and evaporated in vacuo. Silica gel chromatography of the crude residue eluting with diethyl ether in petroleum ether gave the title compound (20 g) as an amber oil.

Workup

  1. waitThe resulting mixture was left
  2. customIt was partitioned between diethyl ether (250 mL) and saturated sodium hydrogen carbonate (150 mL)
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. customevaporated in vacuo
  5. washSilica gel chromatography of the crude residue eluting with diethyl ether in petroleum ether

Sources & evidence

ORD record
ord-002ff63b7cbe4c9483a2082252a1066f
Source dataset
uspto-grants-2007_05
Patent number
US07214674B2

Reaction notes

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