1,3-Propanedithiol → HCID 10104703, compound

HRID 1452954Notes

Reaction equation

HRID 1452954 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.C1C(=O)N(Br)C(=O)C1.[CH2:18]([SH:22])[CH2:19][CH2:20][SH:21]>C(Cl)Cl>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]1[S:22][CH2:18][CH2:19][CH2:20][S:21]1

Participants

5

Reactant 3

HCID 80131,3-PropanedithiolHCID 67184N-bromobutanimideHCID 67970o-Fluorobenzaldehyde

Product 1

HCID 10104703HCID 10104703, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-fluorobenzaldehyde (10.03 g, 80.8 mmol, 1.0 eq.) and NBS (2.16 g, 12.1 mmol, 0.2 eq.) in CH2Cl2 (400 mL) was added 1,3-propanedithiol (9.8 mL, 97.6 mmol, 1.2 eq.). After 0.75 h, the reaction mixture was concentrated in vacuo. The residue was diluted with CH2Cl2 and water, and the layers were separated. The organic layer was dried over Na2SO4, filtered, concentrated in vacuo, and triturated with hexanes to give 2-(2-fluorophenyl)-1,3-dithiane as a white solid (13.55 g, 78% yield).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additionThe residue was diluted with CH2Cl2 and water
  3. customthe layers were separated
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customtriturated with hexanes

Sources & evidence

ORD record
ord-73c51fcdd265420f8035d2e36d5a4ded
Source dataset
uspto-grants-2009_01
Patent number
US07473784B2

Reaction notes

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