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

HRID 1774532

Reaction equation

HRID 1774532 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-23900a84317847b2bbd04e9318cc8f24
Source dataset
uspto-grants-2016_02
Patent number
US09260412B2

Linked notes

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