Benzyl Bromide → HCID 15057657, compound

HRID 654038Notes

Reaction equation

HRID 654038 reaction equation
[Na].[Br:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[C:5]([C:10]([F:13])([F:12])[F:11])[C:4]=1[OH:14].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)C>[Br:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[C:5]([C:10]([F:12])([F:13])[F:11])[C:4]=1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 5360545SodiumHCID 150576562-Bromo-4-fluoro-6-(trifluoromethyl)phenol

Product 1

HCID 15057657HCID 15057657, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.65 g (28 mmol) of sodium is dissolved in 35 ml of dry ethanol, 5.96 g (23 mmol) of 2-bromo-4-fluoro-6-(trifluoromethyl)-phenol is added and it is stirred for 20 minutes at room temperature, 7.17 g (42 mmol) of benzyl bromide is added and refluxed for 1 hour. Sodium bromide precipitates out crystalline from the solution The hot solution is filtered, the filtrate is evaporated to dryness and the residue is chromatographed on silica gel 60 with dichloromethane/hexane. 6.29 g (18 mmol) =78.3% of the theoretical yield is obtained as a predominantly crystalline solid.

Workup

  1. temperaturerefluxed for 1 hour
  2. customSodium bromide precipitates out crystalline from the solution The hot solution
  3. filtrationis filtered
  4. customthe filtrate is evaporated to dryness
  5. customthe residue is chromatographed on silica gel 60 with dichloromethane/hexane
  6. custom6.29 g (18 mmol) =78.3% of the theoretical yield
  7. customis obtained as a predominantly crystalline solid

Sources & evidence

ORD record
ord-5a776d8a143f48ada58d09d7837f5b50
Source dataset
uspto-grants-1992_07
Patent number
US05130119

Reaction notes

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