Boron trifluoride → HCID 59625898, compound

HRID 401716Notes

Reaction equation

HRID 401716 reaction equation
[C:1]([C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(F)(F)F.[CH2:23]([SH:26])[CH2:24][SH:25]>C(Cl)Cl>[C:2]1([C:1]2([C:9]3[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=3)[S:26][CH2:23][CH2:24][S:25]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6356Boron trifluorideHCID 109021,2-EthanedithiolHCID 349620Methyl 4-benzoylbenzoate

Product 1

HCID 59625898HCID 59625898, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 4-benzoylbenzoate 64a (2.08 mmol, 0.50 g) and BF3.(OAc)2 (5.2 mmol, 0.73 mL) were dissolved in dry CH2Cl2 under N2. Ethane-1,2-dithiol (3.95 mmol, 0.333 mL) was added and the solution was stirred overnight. The reaction mixture was partitioned between CH2Cl2 and water. The organic layer was concentrated and purified by flash column chromatography (silica gel, 10% EtOAc/hexanes) to afford compound 64b.

Workup

  1. customThe reaction mixture was partitioned between CH2Cl2 and water
  2. concentrationThe organic layer was concentrated
  3. custompurified by flash column chromatography (silica gel, 10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-88203029957846308d7cf3440724ed06
Source dataset
uspto-grants-2014_06
Patent number
US08741887B2

Reaction notes

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