Methyl iodide → 4-Bromo-2-chloro-1-methanesulfonylbenzene

Hydrazine monohydrate (1.51 mL, 48 mmol) was added to a cooled 0° C. solution of 4-bromo-2-chlorobenzenesulfonyl chloride (5 g, 17.2 mmol) dissolved in THF (50 mL). The reaction was stirred at room temperature for 2 hours and then the solvent was removed in vacuo to give a white solid. The solid was dissolved in EtOH (100 mL) and treated with sodium acetate (6.56 g, 80 mmol) followed by methyl iodide (4.9 mL, 79 mmol). The reaction mixture was refluxed for 18 hours. The solvent was removed in vacuo to give a residue that was partitioned between 1 N HCl and EtOAc. The organic layer was dried over MgSO4 and concentrated. The crude mixture was purified by flash column chromatography to give the product (1.5 g, 32%). 1H NMR (300 MHz, CDCl3): δ 3.26 (s, 3H), 7.63 (dd, J=8.5, 1.9 Hz, 2H), 7.74 (d, J=1.9 Hz, 1H), 8.02 (d, J=8.5 Hz, 1H).

1. customthe solvent was removed in vacuo
2. customto give a white solid
3. temperatureThe reaction mixture was refluxed for 18 hours
4. customThe solvent was removed in vacuo
5. customto give a residue that
6. customwas partitioned between 1 N HCl and EtOAc
7. dry with materialThe organic layer was dried over MgSO4
8. concentrationconcentrated
9. customThe crude mixture was purified by flash column chromatography

ORD record

ord-a15ef25100ca46488f6a0afec8b4ef7d

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07622605B2