Ethyl Bromide → 1,3-Dibromo-5-ethoxymethyl-2-methyl-benzene

Temperature

70 °C

A mixture of (3,5-dibromo-4-methyl-phenyl)-methanol (4 g, 14.288 mmol), 60% NaH (690 mg, 28.75 mmol) and THF (72 mL) was heated to 70° C. in a sealed tube for 15 minutes. The reaction was cooled, bromoethane (3.2 mL, 42.86 mmol) was added and the reaction continued heating at 70° C. for 6 h. The reaction was cooled, poured onto water, extracted with EtOAc (×3). The organics were washed with water, brine and dried (Na2SO4). Chromatography (Hexanes/EtOAc) afforded 1,3-dibromo-5-ethoxymethyl-2-methyl-benzene (2.187 g) as a colourless oil. 1H NMR (400 MHz, d6-DMSO) δ: 1.15 (t, 3H), 2.48 (s, 3H), 3.46 (q, 2H), 4.41 (s, 2H), 7.57 (s, 2H) ppm.

1. temperatureThe reaction was cooled
2. temperaturethe reaction continued heating at 70° C. for 6 h
3. temperatureThe reaction was cooled
4. additionpoured onto water
5. extractionextracted with EtOAc (×3)
6. washThe organics were washed with water, brine
7. dry with materialdried (Na2SO4)

ORD record

ord-8692a9fba2ee403081f5f0a23994fbf5

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08349836B2