Benzyl Bromide → 1,3-Dibromo-5-fluoro-2-(phenylmethoxy)benzene

HRID 654030Notes

Reaction equation

HRID 654030 reaction equation
[Na].[Br:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[C:5]([Br:10])[C:4]=1[OH:11].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Br-].[Na+]>C(O)C>[CH2:12]([O:11][C:4]1[C:3]([Br:2])=[CH:8][C:7]([F:9])=[CH:6][C:5]=1[Br:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 676542,6-Dibromo-4-fluorophenolHCID 253881Sodium BromideHCID 5360545Sodium

Product 1

HCID 150576451,3-Dibromo-5-fluoro-2-(phenylmethoxy)benzene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.21 g (96 mmol) of sodium is dissolved in 66 ml of ethanol with exclusion of moisture. 21.6 g (80 mmol) of 2,6-dibromo-4-fluorophenol is added to this solution. A suspension results. 20.5 g (120 mmol) of benzyl bromide is added to the suspension. It is stirred for 30 minutes at room temperature and then is refluxed for 1 hour. A sample of the suspension then reacts neutrally to moist reaction paper. The precipitate of the sodium bromide is suctioned off, the filtrate is evaporated to dryness and the residue is crystallized from ethanol. 23.7 g (66 mmol)=82.5% of the theoretical yield is obtained as a crystallizate. Melting point 83° C.

Workup

  1. customA suspension results
  2. temperatureis refluxed for 1 hour
  3. customA sample of the suspension then reacts neutrally to moist reaction paper
  4. customthe filtrate is evaporated to dryness
  5. customthe residue is crystallized from ethanol
  6. custom23.7 g (66 mmol)=82.5% of the theoretical yield
  7. customis obtained as a crystallizate

Sources & evidence

ORD record
ord-53d07509cf9d4c8aa2f910f1577888d5
Source dataset
uspto-grants-1992_07
Patent number
US05130119

Reaction notes

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