Water → HCID 59204831, compound

HRID 2241886Notes

Reaction equation

HRID 2241886 reaction equation
[Br:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([O:9]C)=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=2)[CH2:13][CH2:12]1.B(Cl)(Cl)Cl.C(=O)=O.CC(C)=O.O>C(Cl)Cl>[Br:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[N:11]1[CH2:12][CH2:13][N:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:19][N:18]=2)[CH2:15][CH2:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 25135Boron TrichlorideHCID 11662395HCID 11662395, compoundHCID 18522661Acetone cardice

Product 1

HCID 59204831HCID 59204831, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of 0.38 gram (0.00084 mole) of 2-bromo-3-chloro-5-methoxy-1-{4-[5-(trifluoromethyl)(2-pyridyl)]piperazinyl}benzene and 0.78 gram (0.0021 mole) of n-tetrabutylammonium iodide in 30 mL of methylene chloride was cooled in a dry-ice/acetone bath and 2.1 mL (0.0021 mole, a 1.0M solution in methylene chloride) of boron trichloride was added dropwise. Upon completion of addition the reaction mixture was kept cold in the dry-ice/acetone bath for an additional 30-minute period, then it was allowed to warm to ambient temperature where it stirred during a three-hour period. After this time the reaction mixture was cooled in an ice/water bath and 15 mL of water was added. The organic layer was separated and the aqueous layer was extracted with one 15 mL portion of methylene chloride. The organic layer and the extract were combined and dried with sodium sulfate. The mixture was filtered, and the filtrate was concentrated under reduced pressure to a residue. The residue was purified with column chromatography on silica gel using as eluants: 50% hexane in methylene chloride, then 100% methylene chloride, and finally 2% methanol in methylene chloride. The appropriate fractions were combined and concentrated under reduced pressure, yielding 0.17 gram of the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. temperatureAfter this time the reaction mixture was cooled in an ice/water bath
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with one 15 mL portion of methylene chloride
  5. dry with materialdried with sodium sulfate
  6. filtrationThe mixture was filtered
  7. concentrationthe filtrate was concentrated under reduced pressure to a residue
  8. customThe residue was purified with column chromatography on silica gel using as eluants
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ab7f4890cbff4cd990d6504f247c6ee4
Source dataset
uspto-grants-2010_03
Patent number
US07671055B2

Reaction notes

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