Chloroiodomethane → 1-Bromo-4-cyclopropoxybenzene

Temperature

2.5 °C

To a 0° C. solution of 1-bromo-4-vinyloxy-benzene (31.75 g, 159.51 mmol) and chloroiodomethane (101.3 g, 574.2 mmol) in 1,2-dichloroethane (410 mL), slowly add diethylzinc (1 M in heptane, 380 mL) over 1 hr while maintaining the temperature below 5° C. Stir the white mixture at 0-5° C. for 2 hours. Quench the reaction slowly at 5° C. with aqueous saturated ammonium chloride (400 mL, exothermic) and separate the layers. Extract the aqueous layer with diethyl ether (2×200 mL). Combine the organic layers, wash with saturated ammonium chloride (400 ml), dry over sodium sulfate, filter, and concentrate under reduced pressure to give the title compound (33 g, 97%) as an oil: GCMS: 212.

1. customQuench
2. customthe reaction slowly at 5° C. with aqueous saturated ammonium chloride (400 mL, exothermic)
3. customseparate the layers
4. extractionExtract the aqueous layer with diethyl ether (2×200 mL)
5. washCombine the organic layers, wash with saturated ammonium chloride (400 ml)
6. dry with materialdry over sodium sulfate
7. filtrationfilter
8. concentrationconcentrate under reduced pressure

ORD record

ord-3e946c66371a4ec7afd0b0554f7a9758

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08299061B2