2-Methoxybenzaldehyde → (3-Bromo-2-methoxyphenyl)-(2-methoxyphenyl)methanol

HRID 1111285Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[O:9][CH3:10].C([Li])CCC.[CH:16](=[O:25])[C:17]1[C:18]([O:23][CH3:24])=[CH:19][CH:20]=[CH:21][CH:22]=1.[Cl-].[NH4+]>O1CCCC1>[Br:8][C:4]1[C:3]([O:9][CH3:10])=[C:2]([CH:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])[OH:25])[CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: -63 °C

Procedure

2,6-Dibromoanisole (138.0 g, 0.51 mol) was dissolved in 750 ml of tetrahydrofuran and the solution cooled to -63° C. Butyl lithium (319 ml of 1.6 M, 0.51 mol) was added slowly with stirring and the mixture stirred at -60° C. for 4.5 hours and then 69.4 g (0.51 mol) of o-anisaldehyde in 250 ml of tetrahydrofuran was added slowly with stirring and the mixture allowed to stir cold for 1 hour. The mixture was allowed to warm to ambient temperature and was then poured into a mixture of ice and saturated aqueous ammonium chloride. The resulting mixture was extracted with ether and the ether extract dried over magnesium sulfate and then concentrated by evaporation under reduced pressure to obtain the title compound. This was purified by preparative liquid chromatography eluting with a 5:95 mixture of ethyl acetate and hexane to obtain 44.6 g (24 percent of theory) of material having a proton nmr spectrum consistent with the assigned structure.

Workup

stirringthe mixture stirred at -60° C. for 4.5 hours
stirringwith stirring
stirringto stir cold for 1 hour
temperatureto warm to ambient temperature
extractionThe resulting mixture was extracted with ether
extractionthe ether extract
dry with materialdried over magnesium sulfate
concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record: ord-0260b776de2c4eb49e417e6bbff3fa41
Source dataset: uspto-grants-1990_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04979978

Reaction notes

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