Hydrochloric Acid → HCID 16733861, compound

HRID 1015714Notes

Reaction equation

HRID 1015714 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH3:11][S-:12].[Na+].Cl>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:12][CH3:11])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7363275-Bromo-2-fluorobenzaldehydeHCID 4378561Sodium methanethiolate

Product 1

HCID 16733861HCID 16733861, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(Step 1) 5-Bromo-2-fluorobenzaldehyde (15.4 g) and sodium methanethiolate (5.85 g) were stirred in N,N-dimethylformamide (30 ml) at 60° C. for 30 min. The reaction solution was treated with 1N hydrochloric acid, and extracted with ethyl acetate. The extract was washed successively with aqueous sodium hydrogen carbonate solution and saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was crystallized from ethyl acetate-hexane to give 5-bromo-2-(methylsulfanyl)benzaldehyde (11.1 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed successively with aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-4c07cd20634e4b5aa15ffd4923b94c88
Source dataset
uspto-grants-2011_07
Patent number
US07985862B2

Reaction notes

Loading…