Benzyl Bromide → 1-(Benzyloxy)-4-bromo-2-fluorobenzene

HRID 62841

Reaction equation

HRID 62841 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Br:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([F:23])[CH:17]=1>CN(C=O)C>[CH2:7]([O:22][C:19]1[CH:20]=[CH:21][C:16]([Br:15])=[CH:17][C:18]=1[F:23])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 27249814-Bromo-2-fluorophenol

Product 1

HCID 187574911-(Benzyloxy)-4-bromo-2-fluorobenzeneYield 101.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DMF (12 mL), K2CO3(1.19 g, 8.55 mmol) and benzyl bromide (0.75 mL, 6.27 mmol) was added to 4-bromo-2-fluorophenol (1.1 g, 5.7 mmol), and the mixture was stirred at room temperature for 2 hours. After the termination of the reaction, the reactant was concentrated and the residue was diluted with 20 mL water. The mixture was extracted with EtOAc. The organic layer was separated and dried with MgSO4 to obtain the title compound (1.62 g, 100%).

Workup

  1. customAfter the termination of the reaction
  2. concentrationthe reactant was concentrated
  3. additionthe residue was diluted with 20 mL water
  4. extractionThe mixture was extracted with EtOAc
  5. customThe organic layer was separated
  6. dry with materialdried with MgSO4

Sources & evidence

ORD record
ord-02bc1bb165664703bc47e99c5b59c704
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Linked notes

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