Sulfuryl chloride → 2-Chloro-6-fluorobenzothiazole

HRID 887400Notes

Reaction equation

HRID 887400 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7](S)[S:8][C:4]=2[CH:3]=1.S(Cl)([Cl:15])(=O)=O>C(Cl)Cl>[Cl:15][C:7]1[S:8][C:4]2[CH:3]=[C:2]([F:1])[CH:11]=[CH:10][C:5]=2[N:6]=1

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 178505461HCID 178505461, compound

Product 1

HCID 20498702-Chloro-6-fluorobenzothiazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

6-fluorobenzo[d]thiazole-2-thiol (14.0 g, 0.075 mol) was suspended in dry DCM (100 mL) under nitrogen and cooled to 0° C. Sulfuryl chloride (18.5 mL) was then added dropwise and the reaction was allowed to warm to RT and stirred for 1 h. The reaction mixture was then poured on to crushed ice and extracted with DCM (4×300 mL). The combined organic extract was given brine wash (2×150 mL), dried (Na2SO4) and concentrated. The crude compound was purified by column chromatography (Silica 100-200 mesh; 3-7% ethyl acetate in hexane) to provide 2-chloro-6-fluorobenzo[d]thiazole as a white solid.

Workup

  1. temperatureto warm to RT
  2. additionThe reaction mixture was then poured on
  3. customto crushed ice
  4. extractionextracted with DCM (4×300 mL)
  5. extractionThe combined organic extract
  6. washwash (2×150 mL)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe crude compound was purified by column chromatography (Silica 100-200 mesh; 3-7% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-88e179e5d536404da73822e9491e2e36
Source dataset
uspto-grants-2012_08
Patent number
US08247418B2

Reaction notes

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