Boron Trichloride → HCID 67364518, compound

HRID 1913304Notes

Reaction equation

HRID 1913304 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([O:9][C:10]([F:13])([F:12])[F:11])[CH:6]=[CH:5][C:4]=1[C:14](=[O:16])[CH3:15].B(Cl)(Cl)Cl>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[C:7]([O:9][C:10]([F:11])([F:12])[F:13])[CH:6]=[CH:5][C:4]=1[C:14](=[O:16])[CH3:15]

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 35934932'-Methoxy-4'-(trifluoromethoxy)acetophenone

Product 1

HCID 67364518HCID 67364518, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-(2-methoxy-4-(trifluoromethoxy)phenyl)ethanone (17.8 g, 76.0 mmol) in CH2Cl2 (178 mL) was cooled to −25° C. and boron trichloride (91.0 mL of a 1.0 M solution in CH2Cl2, 91 mmol) was added dropwise keeping the internal temperature ≦−18° C. Following addition, analysis by LCMS indicated complete reaction. The reaction mixture was poured into ice (75 g) and partitioned. The organic layer was washed with water (50 mL), dried (Na2SO4), filtered, and concentrated to give 16.2 g (73.6 mmol, 97% yield) of the title compound. MS (DCI/NH3) m/z 238 (M+NH4)+.

Workup

  1. customthe internal temperature ≦−18° C
  2. additionaddition, analysis by LCMS
  3. customreaction
  4. custompartitioned
  5. washThe organic layer was washed with water (50 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d9ee3e104b2743dbb5188d2d980dbb5f
Source dataset
uspto-grants-2013_12
Patent number
US08609692B2

Reaction notes

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