Hydrogen Bromide → 2-(Bromomethyl)-5-(difluoromethoxy)-1,3-difluorobenzene

HRID 1484684Notes

Reaction equation

HRID 1484684 reaction equation
[F:1][CH:2]([F:14])[O:3][C:4]1[CH:9]=[C:8]([F:10])[C:7]([CH2:11]O)=[C:6]([F:13])[CH:5]=1.[BrH:15]>C(OCC)C>[Br:15][CH2:11][C:7]1[C:8]([F:10])=[CH:9][C:4]([O:3][CH:2]([F:14])[F:1])=[CH:5][C:6]=1[F:13]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 69140944Benzenemethanol, 4-(difluoromethoxy)-2,6-difluoro-

Product 1

HCID 867324312-(Bromomethyl)-5-(difluoromethoxy)-1,3-difluorobenzeneYield 67%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

162 mg [4-(difluoromethoxy)-2,6-difluorophenyl]methanol (0.769 mmol, 1.0 eq.) were dissolved in 0.348 mL hydrogen bromide (2.12 mmol, 2.8 eq.). and stirred at rt over night. The reaction mixture was diluted with diethylether and stirred for 5 minutes. The aqueous layer was washed twice with diethylether. The combined organic layers were washed with brine, dried over a silicon filter and concentrated in vacuo to provide the 149 mg (0.51 mmol, 67%) of the crude product, which was used without further purification.

Workup

  1. stirringstirred for 5 minutes
  2. washThe aqueous layer was washed twice with diethylether
  3. washThe combined organic layers were washed with brine
  4. customdried over a silicon
  5. filtrationfilter
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f4794655fd6a4886a308cec0c6a0f560
Source dataset
uspto-grants-2016_08
Patent number
US09422268B2

Reaction notes

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