Water → 2-Chloro-6-(methylthio)benzaldehyde

HRID 502606Notes

Reaction equation

HRID 502606 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6](Cl)[C:3]=1[CH:4]=[O:5].[CH3:11][S-:12].[Na+].O>CN(C)C=O>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([S:12][CH3:11])[C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 67372,6-DichlorobenzaldehydeHCID 4378561Sodium methanethiolate

Product 1

HCID 571961882-Chloro-6-(methylthio)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,6-dichlorobenzaldehyde (20 g, 114.28 mmol) in N,N-dimethylformamide (200 ml), sodium thiomethoxide (8.81 g, 125.7 mmol) was added at 0° C. The reaction mixture was allowed to warm to room temperature overnight, then poured into water. A yellow precipitate was collected by vacuum filtration and dried to afford 2-chloro-6-(methylthio)benzaldehyde (11. g), as a light yellow solid. (This method is general for other 2-haloaldehydes). 1H NMR (300 MHz, CDCl3): 10.6 (s, 1H), 7.4 (t, 1H), 7.2 (dd, 2H), 2.4 ppm (s, 3H). MW=187 confirmed by LC-MS, tr=13.18 min (Method Y) MH+=188.

Workup

  1. filtrationA yellow precipitate was collected by vacuum filtration
  2. customdried

Sources & evidence

ORD record
ord-ee6a64fe5d1d4554a1ae7be8b4a1ab8c
Source dataset
uspto-grants-2010_08
Patent number
US07776847B2

Reaction notes

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