Boron trifluoride → HCID 59238222, compound

HRID 1359924Notes

Reaction equation

HRID 1359924 reaction equation
[Br:1][C:2]1[C:3]([CH3:19])=[C:4]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][CH:12]=2)=O)[CH:5]=[C:6]([I:8])[CH:7]=1.C([SiH](CC)CC)C.B(F)(F)F.[OH-].[K+].C(OC(C)C)(C)C>ClCCl.C(#N)C>[Br:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[C:4]([CH2:9][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][CH:12]=2)[C:3]=1[CH3:19]

Participants

8

Reactant 5

HCID 6356Boron trifluorideHCID 7914Diisopropyl EtherHCID 12052TriethylsilaneHCID 14797Potassium HydroxideHCID 59238233HCID 59238233, compound

Product 1

HCID 59238222HCID 59238222, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (3-bromo-5-iodo-2-methyl-phenyl)-(4-ethyl-phenyl)-methanone (4.2 g) and triethylsilane (4.7 mL) in dichloromethane (10 mL) and acetonitrile (28 mL) is cooled in an ice-bath. Then, boron trifluoride diethyletherate (1.4 mL) is added dropwise over 3 min. The solution is stirred for 14 h at ambient temperature, before an aqueous 25% solution of KOH and diisopropylether are added. The organic phase is separated and the aqueous phase is extracted three times with diisopropylether. The combined organic phases are washed with 2 M potassium hydroxide solution and brine and then dried (sodium sulphate). After the solvent is evaporated, the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 1:0->1:1).

Workup

  1. additionare added
  2. customThe organic phase is separated
  3. extractionthe aqueous phase is extracted three times with diisopropylether
  4. washThe combined organic phases are washed with 2 M potassium hydroxide solution and brine
  5. dry with materialdried (sodium sulphate)
  6. customAfter the solvent is evaporated
  7. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 1:0->1:1)

Sources & evidence

ORD record
ord-2349a904db3a4ca4b48f369c94d878ac
Source dataset
uspto-grants-2011_02
Patent number
US07879807B2

Reaction notes

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