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

HRID 2390131Notes

Reaction equation

HRID 2390131 reaction equation
CS([O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[C:9]([F:14])[CH:8]=1)(=O)=O.N1C(C)=CC=C[C:16]=1C>CO.CCOCC>[Br:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][O:5][CH3:16])=[CH:8][C:9]=1[F:14]

Participants

5

Reactant 2

HCID 79372,6-Lutidine2×HCID 58522007HCID 58522007, compound2×

Product 1

HCID 205916621-Bromo-2-fluoro-4-(methoxymethyl)benzene

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 4-bromo-3-fluorobenzyl methanesulfonate (Intermediate 18, 286 mg; 1.01 mmol) and 2,6-lutidine (234 μL; 2.0 mmol) in methanol (4 mL) was stirred for 16 hours at RT. Additional aliquots of 2,6-lutidine (234 μL; 2.0 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 in a mixture with ethyl ether.

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-d6489737d15d47ac81cfc2f69730bf79
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

Loading…