Boron trifluoride → HCID 59625898, compound

HRID 403305Notes

Reaction equation

HRID 403305 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 18a (0.50 g, 2.08 mmol) and BF3.(OAc)2 (0.73 mL, 5.2 mmol) were dissolved in dry CH2Cl2 under a N2 atmosphere. Ethane-1,2-dithiol (0.333 mL, 3.95 mmol) 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 18b.

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-ef6440b5428b405f822e23364f41be60
Source dataset
uspto-grants-2014_06
Patent number
US08748417B2

Reaction notes

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