Methyl iodide → HCID 58071403, compound

Temperature

30 °C

To a homogeneous CH3CN (200 mL) solution of 4,6-dibromo-2-fluoro-3-methylphenol (2, 28.4 g, 100 mmol) at rt, K2CO3 (16.59 g, 120 mmol) was added, followed by MeI (9.3 mL, 150 mmol). The cloudy solution was stirred at 30° C. overnight. The reaction went to completion monitored by LC and TLC. The mixture was cooled to rt, quenched by addition of H2O (100 mL) and sat. aq. NH4Cl (100 mL), two layers were mixed well and then separated, aqueous layer was extracted with EtOAc (50 mL), organic layers were combined, dried (MgSO4), filtered, solvent was removed in vacuo. The crude product, an oil, was dissolved in CH2Cl2 (˜80 mL) and the solution was passed through a silica gel pad (˜50 g of silica gel), washing with CH2Cl2 (˜100 mL). The filtrate was collected, and the solvent was removed in vacuo. 1,5-Dibromo-3-fluoro-2-methoxy-4-methylbenzene was obtained as a solid: 31.62 g (>99% yield); 1H NMR (300 MHz, CDCl3) δ 7.53 (d, J=2.1, 1H), 3.92 (s, 3H), 2.29 (d, J=2.8, 3H).

1. temperatureThe mixture was cooled to rt
2. customquenched by addition of H2O (100 mL) and sat. aq. NH4Cl (100 mL), two layers
3. additionwere mixed well
4. customseparated
5. extractionaqueous layer was extracted with EtOAc (50 mL), organic layers
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. customsolvent was removed in vacuo
9. dissolutionThe crude product, an oil, was dissolved in CH2Cl2 (˜80 mL)
10. washwashing with CH2Cl2 (˜100 mL)
11. customThe filtrate was collected
12. customthe solvent was removed in vacuo

ORD record

ord-409934c5dc054bc680dc994d41deb47e

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08343954B2