Hexane → 1-Bromo-3,4-diethoxy-2-fluorobenzene

HRID 2223754Notes

Reaction equation

HRID 2223754 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:13]=1[O:19][CH2:20][CH3:21])[CH3:10].CCCCCC>C(#N)C>[Br:1][C:15]1[CH:16]=[CH:17][C:12]([O:11][CH2:9][CH3:10])=[C:13]([O:19][CH2:20][CH3:21])[C:14]=1[F:18]

Participants

5

Reactant 3

HCID 8058HexaneHCID 67184N-bromobutanimideHCID 224601261,2-Diethoxy-3-fluorobenzene

Product 1

HCID 230937081-Bromo-3,4-diethoxy-2-fluorobenzeneYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of N-bromosuccinimide (NBS) (153.72 g, 864 mmol) in acetonitrile (1.5 L) was added dropwise to a solution of 1,2-diethoxy-3-fluorobenzene (150.00 g, 814 mmol) in acetonitrile (900 mL) on ice, and this was stirred at room temperature overnight. After the solvent was distilled off, ethyl acetate was added to the residue and washed with water. The obtained aqueous layer was extracted again with ethyl acetate, and the extract was combined with the aforementioned organic layer. The organic layer was washed sequentially with water, saturated brine, and water again, and was dried over anhydrous magnesium sulfate. The solution was concentrated and an oily substance was obtained. Following hexane addition to the oily substance, crystals that have precipitated were removed by filtration. The remaining solution was concentrated to yield an oily substance, which was distilled under reduced pressure to obtain 205.65 g of the subject compound (yield: 96%).

Workup

  1. distillationAfter the solvent was distilled off
  2. additionethyl acetate was added to the residue
  3. washwashed with water
  4. extractionThe obtained aqueous layer was extracted again with ethyl acetate
  5. washThe organic layer was washed sequentially with water, saturated brine, and water again
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. concentrationThe solution was concentrated
  8. customan oily substance was obtained
  9. customhave precipitated
  10. customwere removed by filtration
  11. concentrationThe remaining solution was concentrated
  12. customto yield an oily substance, which
  13. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-afc65552edce46f094f476c9d6c46347
Source dataset
uspto-grants-2008_05
Patent number
US07375236B2

Reaction notes

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