Toluene → 3-Chloro-5-methoxyphenol

温度

-78 °C

1-Chloro-3,5-dimethoxy-benzene (1.72 g, 10 mmol) in 10 mL of CH2Cl2 was cooled to −78° C., followed by 1.0 M BBr3 in toluene (10 mL, 10 mmol) added dropwise. The solution was stirred at −78° C. for 1 hour, and then allowed to warmed to room temperature over 2 hours. The reaction was quenched with water, and the aqueous layer was extracted with additional CH2Cl2. The combined organic layers were washed with brine, dried, and concentrated under pressure. The residue was purified by silica gel column chromatography eluting with 1:1 EtOAc/Hexanes to give 0.51 g of the title compound. MS (APCI) m/e 159 (M+H)+, 1H NMR (500 MHz, DMSO-d6): □ 9.88 (s, 1H), 6.43 (m, 1H), 6.39 (m, 1H), 6.28 (m, 1H), 3.70 (s, 3H).

1. additionadded dropwise
2. temperatureallowed to warmed to room temperature over 2 hours
3. customThe reaction was quenched with water
4. extractionthe aqueous layer was extracted with additional CH2Cl2
5. washThe combined organic layers were washed with brine
6. customdried
7. concentrationconcentrated under pressure
8. customThe residue was purified by silica gel column chromatography
9. washeluting with 1:1 EtOAc/Hexanes

ORDレコード

ord-5b6fa880f6dd4232b7b7109137d830c8

出典データセット

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07456169B2