Boron trifluoride etherate → 2-[1,3-Dithian-2-yl]-5-nitrobenzoic acid

HRID 280708

Reaction equation

HRID 280708 reaction equation
O[CH:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[C:4](=[O:14])[O:3]1.[CH2:15]([SH:19])[CH2:16][CH2:17][SH:18].B(F)(F)F.CCOCC.S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)(Cl)Cl>[S:18]1[CH2:17][CH2:16][CH2:15][S:19][CH:2]1[C:10]1[CH:9]=[CH:8][C:7]([N+:11]([O-:13])=[O:12])=[CH:6][C:5]=1[C:4]([OH:3])=[O:14]

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 80131,3-PropanedithiolHCID 24083Sulfuric acid magnesium salt (1:1)HCID 5226713-Hydroxy-6-nitroisobenzofuran-1(3h)-one

Product 1

HCID 135302822-[1,3-Dithian-2-yl]-5-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To an ice-cooled mixture of the Compound 3a (5.00 g, 25.6 mmol) and propane-1,3-dithiol (2.92 g, 27 mmol) in chloroform (75 mL) was added boron trifluoride etherate (2 mL). The mixture was stirred and allowed to warm to room temperature. After stirring for 3 hours, most of the solid had dissolved. Magnesium sulfate was added to dry the solution, and stirring was continued overnight. Filtration and evaporation of the solvent afforded a light yellow solid. This material was triturated with butyl chloride to give the Compound 3b; m.p. 192°-194° C.; 1H NMR (CDCl3 +MeSO-d6 +D2O)δ1.8-2.3 (m, 2H, CH2CH2CH2, 2.9-3.2 (m, 4H, --CH2CH2CH2 --), 6.56 (s, 1H, --SCHS--), 7.6-8.8 (m, 3H, ArH).

Workup

  1. stirringAfter stirring for 3 hours, most of the solid
  2. dissolutionhad dissolved
  3. customto dry the solution
  4. stirringstirring
  5. filtrationFiltration and evaporation of the solvent
  6. customafforded a light yellow solid
  7. customThis material was triturated with butyl chloride

Sources & evidence

ORD record
ord-e75ce6118e234a7c96dfcb2fd7ee39e8
Source dataset
uspto-grants-1986_05
Patent number
US04590276

Linked notes

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