Boron trifluoride → HCID 59625898, compound

HRID 2365689Notes

Reaction equation

HRID 2365689 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-fe353b6d2e10429bb3da13d06e09795c
Source dataset
uspto-grants-2014_04
Patent number
US08697683B2

Reaction notes

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