2,6-Lutidine → 2-bromo-1-fluoro-4-(methoxymethyl)benzene

HRID 2390117Notes

Reaction equation

HRID 2390117 reaction equation
CS([O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([Br:14])[CH:8]=1)(=O)=O.N1C(C)=CC=C[C:16]=1C>CO.CCOCC>[Br:14][C:9]1[CH:8]=[C:7]([CH2:6][O:5][CH3:16])[CH:12]=[CH:11][C:10]=1[F:13]

Participants

5

Reactant 2

HCID 79372,6-Lutidine2×HCID 598548133-Bromo-4-fluorobenzyl methanesulfonate2×

Product 1

HCID 27694162-bromo-1-fluoro-4-(methoxymethyl)benzene

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 3-bromo-4-fluorobenzyl methanesulfonate (Intermediate 14, 330 mg; 1.17 mmol) and 2,6-lutidine (176 μL; 1.52 mmol) in methanol (4 mL) was stirred for 16 hours at RT. Additional aliquots of 2,6-lutidine (176 μL; 1.52 mmol each) were added once a day for a total of three days, during which stirring was continued at RT. The mixture was taken up in Et2O, washed with water, HCl (0.1N in water) and brine. The organic phase was dried over MgSO4, filtered and concentrated with moderate vacuum and without heating affording the title compound as a pale yellow liquid.

Workup

  1. customwas continued at RT
  2. washwashed with water, HCl (0.1N in water) and brine
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated with moderate vacuum
  6. temperaturewithout heating

Sources & evidence

ORD record
ord-0fa7fe3286ef40afb92e0df3e99df149
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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