Hydrochloric Acid → 1-(3-Bromophenyl)ethanol

Temperature

-78 °C

Commercially available 3-bromobenzaldehyde (5.0 g, 27 mmol) was dissolved in anhydrous dichloromethane (200 mL) under a dry nitrogen atmosphere and cooled in a dry ice/acetone bath to −78° C. Trimethyl aluminum 2M solution in toluene (16.2 mL, 32 mmol) was added dropwise. After 0.5 h the reaction mixture was allowed to warm to room temperature during which time the cloudiness of the reaction resolved to a clear yellow solution which then proceeded to a colorless solution. After stirring for 1 h at room temperature the reaction mixture was cooled in an ice bath and 1N HCl (100 mL) was added dropwise. The reaction mixture was transferred to a separatory funnel and the organic layer was isolated, dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The crude product was purified by silica gel flash column chromatography eluting with 1:1 Ethyl acetate/hexane to provide 5.4 g (99%) of A4.1a as a colorless oil. LCMS (M+H−OH)+=183, 185

1. temperatureto warm to room temperature during which time the cloudiness of the reaction
2. temperaturewas cooled in an ice bath
3. customThe reaction mixture was transferred to a separatory funnel
4. customthe organic layer was isolated
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltered
7. customevaporated under reduced pressure
8. customThe crude product was purified by silica gel flash column chromatography
9. washeluting with 1:1 Ethyl acetate/hexane
10. customto provide 5.4 g (99%) of A4.1a as a colorless oil

ORD record

ord-6501b3efb6054b4894e49e14a68f3c72

Source dataset

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07456194B2