Methyl iodide → 2-Bromo-5-methoxy-1,3-dimethylbenzene

Temperature

40 °C

A solution of 4-bromo-3,5-dimethylphenol (1.00 g, 4.97 mmol) in acetone (40 mL) was treated with solid CsCO3 (1.17 g, 4.97 mmol) and methyl iodide (0.310 mL, 4.97 mmol) and heated to 40° C. for 3 h. Additional methyl iodide (0.310 mL, 4.97 mmol) was added over the course of the reaction to replace that lost to evaporation. The acetone was removed in vacuo. The resulting white solid residue was partitioned between water and CH2Cl2. The layers were separated and the aqueous layer was further extracted with CH2Cl2 (2×25 mL). The combined organic layers were washed with water (1×25 mL) and dried over MgSO4. The solvent was removed in vacuo to afford the product 2-bromo-5-methoxy-1,3-dimethyl-benzene (1.01 g, 94%) as a colorless oil, which slowly solidified upon standing. 1H NMR (CDCl3): δ 6.644 (s, 2H), 3.762 (s, 3H), 2.382 (s, 6H).

1. customthat lost to evaporation
2. customThe acetone was removed in vacuo
3. customThe resulting white solid residue was partitioned between water and CH2Cl2
4. customThe layers were separated
5. extractionthe aqueous layer was further extracted with CH2Cl2 (2×25 mL)
6. washThe combined organic layers were washed with water (1×25 mL)
7. dry with materialdried over MgSO4
8. customThe solvent was removed in vacuo

ORD record

ord-25733c403a49425793023acf9517bf0f

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07138530B2