1,3-Dibromo-5-fluorobenzene → 3,5-Dibromoanisole

HRID 602587Notes

Reaction equation

HRID 602587 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[C:4]([Br:9])[CH:3]=1.[CH3:10][O:11][Na]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([O:11][CH3:10])[CH:5]=[C:4]([Br:9])[CH:3]=1

Participants

4

Reactant 2

HCID 1370031,3-Dibromo-5-fluorobenzeneHCID 178418582HCID 178418582, compound

Product 1

HCID 110218123,5-Dibromoanisole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

step 1—A solution of 1,3-dibromo-5-fluoro-benzene (CASRN 1435-51-4), MeONa (1 equivalent) and DMF were stirred overnight under an N2 atmosphere at RT. The volatile solvents were removed in vacuo and the residue partitioned between Et2O and water. The organic phase was washed with 5% NaOH, water and brine, dried (MgSO4), filtered and evaporated to afford 1,3-dibromo-5-methoxy-benzene.

Workup

  1. customThe volatile solvents were removed in vacuo
  2. customthe residue partitioned between Et2O and water
  3. washThe organic phase was washed with 5% NaOH, water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-b2581cad6f854ce093e96d2eb8cc70ad
Source dataset
uspto-grants-2011_03
Patent number
US07906540B2

Reaction notes

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