Potassium Carbonate → 1-Bromo-3-iodo-5-(4-methoxy-benzyloxy)-benzene

温度

0 °C

3-Bromo-5-iodo-phenol (8.48 g, 28.37 mmol) was dissolved in DMF (50 mL) under dry argon and cooled to 0° C. Then potassium carbonate (3.92 g, 28.37 mmol) was added, followed by drop wise addition of 4-methoxybenzyl chloride (3.7 mL, 27.0 mmol). The mixture was slowly warmed to room temperature and stirred for 20 h. Additional 4-methoxybenzyl chloride (0.19 mL, 1.4 mmol) was added and the mixture was stirred for additional 24 h at room temperature. The reaction mixture was diluted with tert-butylmethyl ether (300 mL) and water (150 mL). The layers were separated and the aqueous one extracted with tert-butylmethyl ether (2×150 mL). The combined organics were washed with water and brine (150 mL), dried (Na2SO4) and concentrated to give the crude product which was purified by flash chromatography on silica gel (330 g, AcOEt/heptane 1:9). 1-Bromo-3-iodo-5-(4-methoxy-benzyloxy)-benzene (8.80 g, 59%, purity 80%, HPLC 220 nm) was obtained as a yellow oil.

1. temperatureThe mixture was slowly warmed to room temperature
2. stirringthe mixture was stirred for additional 24 h at room temperature
3. customThe layers were separated
4. extractionthe aqueous one extracted with tert-butylmethyl ether (2×150 mL)
5. washThe combined organics were washed with water and brine (150 mL)
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated
8. customto give the crude product which
9. customwas purified by flash chromatography on silica gel (330 g, AcOEt/heptane 1:9)

ORDレコード

ord-c5c30b34a447446bb1f71cc9561ce8c5

出典データセット

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07504401B2