Water → 5-Bromo-2-[(2R)-oxiran-2-ylmethoxy]benzaldehyde

HRID 1584891Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].C1(C)C=CC(S(O[CH2:21][C@@H:22]2[O:24][CH2:23]2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:21][C@@H:22]2[O:24][CH2:23]2)=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 5-bromo-2-hydroxybenzaldehyde (68.75 g), (R)-glycidyl 4-toluenesulphonate (65 g) and potassium carbonate (47.3 g) in dry dimethylformamide (1.5 L) was stirred and heated at 60° C. under nitrogen for 24 hours, then cooled and allowed to stand at ambient temperature for 24 hours. The mixture was poured into water (2 L) then extracted with ether (4×400 ml). The combined extracts were washed with brine (4×500 ml), dried over magnesium sulphate, and the solvent removed in vacuo to give an oil which was purified by flash chromatography over silica eluting with a 4:1 mixture of petroleum ether (b.p. 60-80° C.) and ethyl acetate. Appropriate fractions were combined and the solvent removed in vacuo to give an oil, which on trituration with ether (150 ml) gave (R)-5-bromo-2-(2,3-epoxypropoxy)benzaldehyde as a colourless solid (43.3 g).

Workup

temperaturecooled
extractionthen extracted with ether (4×400 ml)
washThe combined extracts were washed with brine (4×500 ml)
dry with materialdried over magnesium sulphate
customthe solvent removed in vacuo
customto give an oil which
customwas purified by flash chromatography over silica eluting with a 4:1 mixture of petroleum ether (b.p. 60-80° C.) and ethyl acetate
customthe solvent removed in vacuo
customto give an oil, which on trituration with ether (150 ml)

Sources & evidence

ORD record: ord-fa215ccf9b714faeb87748fcd96be4da
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05935973

Reaction notes

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