4-Bromobenzyl alcohol → 1-BroMo-4-(fluoroMethyl)-benzene

HRID 1663601Notes

Reaction equation

HRID 1663601 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]O)=[CH:4][CH:3]=1.COCCN(S(F)(F)[F:20])CCOC>C(Cl)Cl>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][F:20])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 701194-Bromobenzyl alcoholHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluoride

Product 1

HCID 6431801-BroMo-4-(fluoroMethyl)-benzeneYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromobenzylalcohol (561 mg) in methylene chloride (3 mL) was added [bis-(2-methoxyethyl)amino]sulfur trifluoride (590 μL) over a period of 5 minutes under ice-cooling and the mixture was stirred at the same temperature for 1 hours and then stirred at room temperature for 1 hour. The reaction mixture was concentrated in vacuo and the resultant crude product was purified by a column chromatography on silica gel (solvent; hexane/ethyl acetate=100:0→95:5) to give 1-bromo-4-fluoromethyl-benzene (340 mg, yield: 60%).

Workup

  1. temperaturecooling
  2. stirringstirred at room temperature for 1 hour
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe resultant crude product was purified by a column chromatography on silica gel (solvent; hexane/ethyl acetate=100:0→95:5)

Sources & evidence

ORD record
ord-3114292d31324f50a0bc46f594e121c2
Source dataset
uspto-grants-2011_10
Patent number
US08034949B2

Reaction notes

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