Methyl iodide → 1-Bromo-2-chloro-4-methylsulfanyl-benzene

HRID 2264939Notes

Reaction equation

HRID 2264939 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][C:3]=1[Cl:9].[H-].[Na+].I[CH3:13]>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:13])=[CH:4][C:3]=1[Cl:9]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 509980044-Bromo-3-chlorobenzenethiol

Product 1

HCID 595965971-Bromo-2-chloro-4-methylsulfanyl-benzeneYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-Bromo-3-chloro-benzenethiol (0.94 g, 4.21 mmol) was dissolved in tetrahydrofuran (10 ml) and cooled to 0° C. under argon. Sodium hydride (0.19 g, 4.63 mmol) was added and the mixture was stirred for 5 minutes, then iodomethane (0.28 ml, 4.42 mmol) was added. The mixture was allowed to warm, stirring for 30 minutes, then the reaction was quenched with saturated aqueous ammonium chloride. The mixture was extracted with dichloromethane (×2) and the combined organic layers were dried (MgSO4) and concentrated. Purification of the resultant residue by flash chromatography (Si-PCC, pentane) afforded the title compound as a colourless oil (0.65 g, 65%). 1H NMR (CDCl3 400 MHz) 2.47 (3H, s), 6.99 (1H, dd, J=8.45, 2.26 Hz), 7.30 (1H, d, J=2.25 Hz), 7.48 (1H, d, J=8.45 Hz).

Workup

  1. temperatureto warm
  2. stirringstirring for 30 minutes
  3. customthe reaction was quenched with saturated aqueous ammonium chloride
  4. extractionThe mixture was extracted with dichloromethane (×2)
  5. dry with materialthe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated
  7. customPurification of the resultant residue by flash chromatography (Si-PCC, pentane)

Sources & evidence

ORD record
ord-a904be47cac248f7a7a8e86401e97219
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

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