Allyl chloride → 1-Bromo-2-methyl-4-(2-propen-1-yloxy)benzene

Temperature

70 °C

To a dark yellow solution of 4-bromo-3-methyl-phenol (4.68 g, 25 mmol) in isopropanol (60 mL) and 3 N aq. NaOH (20 mL), allylchloride (8.18 g, 107 mmol) is added. The mixture is stirred at 70° C. for 3 h before it is cooled to rt, diluted with diethyl ether and washed with 1 N aq. NaOH solution (275 mL) and 1 M aq. HCl solution (70 mL) followed by brine (70 mL). The org. extract is dried over MgSO4, filtered, concentrated and dried to give crude 4-allyloxy-1-bromo-2-methyl-benzene (5.67 g) as a yellow oil; LC-MS: tR=0.59 min; [M+1]+=not detectable; 1H NMR (CDCl3): δ 2.38 (s, 3H), 4.52 (dt, J=5.3, 1.5 Hz, 2H), 5.29-5.34 (m, 1H), 5.39-5.46 (m, 1H), 6.00-6.11 (m, 1H), 6.65 (dd, J=8.8, 3.0 Hz, 1H), 6.83 (d, J=3.0 Hz, 1H), 7.41 (d, J=8.5 Hz, 1H).

1. temperatureis cooled to rt
2. washwashed with 1 N aq. NaOH solution (275 mL) and 1 M aq. HCl solution (70 mL)
3. extractionextract
4. dry with materialis dried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated
7. customdried

ORD record

ord-2168fe0a138c4dcabc0788242e27ef30

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08592460B2