Bromine → HCID 86682804, compound

HRID 1504328Notes

Reaction equation

HRID 1504328 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[CH2:13][OH:14].[Br:15]Br>S(=O)(=O)(O)O.O.S([O-])([O-])(=O)=O.[Ag+2]>[Br:15][C:6]1[C:5]([O:8][C:9]([F:11])([F:12])[F:10])=[CH:4][C:3]([CH2:13][OH:14])=[C:2]([Cl:1])[CH:7]=1

Participants

6

Reactant 2

HCID 24408BromineHCID 71744207HCID 71744207, compound

Product 1

HCID 86682804HCID 86682804, compoundYield 27.3%

Reagents, catalysts & solvents 3

HCID 178418844HCID 178418844, compoundCatalystHCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

To a solution of (2-chloro-5-trifluoromethoxy-phenyl)-methanol (16.3 g, 71.94 mmol) in sulfuric acid (200 mL) and water (60 mL) was added bromine (12.65 g, 79.13 mmol), followed by silver sulfate (12.34 g, 39.57 mmol). The reaction mixture was stirred at RT for 1 h, poured onto ice, and then extracted with EtOAc (3×100 mL). The organic layers were combined, dried over Na2SO4 and concentrated to afford crude product, which was purified by flash chromatography (0-10% EtOAc in petroleum ether) to give the title intermediate (6.0 g, 27% yield). (m/z): [M−OH]+ calcd for C8H5BrClF3O2 286.91; 288.91. found 289.0.

Workup

  1. additionpoured onto ice
  2. extractionextracted with EtOAc (3×100 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto afford crude product, which
  6. customwas purified by flash chromatography (0-10% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-9c0f8639466e4538bba5d763f3fbf189
Source dataset
uspto-grants-2015_12
Patent number
US09212168B2

Reaction notes

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