Hydrogen Bromide → 1-Bromo 4-fluoronaphthalene

HRID 1743996Notes

Reaction equation

HRID 1743996 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[Br:12]Br.Br>C(Cl)(Cl)(Cl)Cl>[Br:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([F:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 94501-FluoronaphthaleneHCID 24408Bromine

Product 1

HCID 676471-Bromo 4-fluoronaphthalene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a 50 mL round-bottomed flask equipped with condenser and N2 inlet were added 3.75 mL (5.0 g, 34.25 mmol) 1-fluoronaphthalene and 10 mL carbon tetrachloride, followed by dropwise addition of 1.7 mL (5.5 g., 34.375 mmol) bromine over 3 min. The reaction was heated to 50-60° C. as HBr was evolved for 2 hours, then cooled and concentrated. The residue was dissolved in methanol and kept overnight at 0° C. After filtration with cold methanol, the product, with mp close to room temperature, was 4.62 g (60%) of a yellow oil.

Workup

  1. customTo a 50 mL round-bottomed flask equipped with condenser and N2 inlet
  2. temperaturecooled
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in methanol
  5. waitkept overnight at 0° C
  6. filtrationAfter filtration with cold methanol
  7. customthe product, with mp close to room temperature

Sources & evidence

ORD record
ord-e8ed51d56b7a4151a337a7cc942be095
Source dataset
uspto-grants-2006_03
Patent number
US07012078B2

Reaction notes

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