Carbon tetrabromide → 2-(5-Bromo-1,3-oxazol-2-yl)propan-2-yloxy-tert-butylsilane

HRID 1520479Notes

Reaction equation

[C:1]([SiH2:5][O:6][C:7]([CH3:14])([CH3:13])[C:8]1[O:9][CH:10]=[CH:11][N:12]=1)([CH3:4])([CH3:3])[CH3:2].C(Br)(Br)(Br)[Br:16]>O1CCCC1.[Cl-].[NH4+]>[Br:16][C:10]1[O:9][C:8]([C:7]([CH3:14])([CH3:13])[O:6][SiH2:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[N:12][CH:11]=1

Participants

Conditions

Temperature: -40 °C

Procedure

To a solution of 2-(tert-Butyl-dimethyl-silanyloxymethyl)-oxazole) (0.35 g, 1.643 mmol) in dry tetrahydrofuran (8 mL) is added n-Butyl litihum (0.26 g, 4.107 mmol) drop wise under nitrogen atmosphere at −78° C. then stirred at −40° C. for 2 hours. The reaction mixture is again cooled to −78° C. then added carbontetrabromide (1.36 g, 4.107 mmol) and stirred to room temperature for 14 hours. Reaction mixture is diluted with saturated ammonium chloride solution and extracted with ethyl acetate. Organic layer is dried over sodium sulphate, solvent is evaporated in vacuo and purified by column chromatography eluting 2% Ethyl acetate in hexane to afford the crude title compound (0.18 g), which is used in the next step without purification. LC-MS (m/z): [M+H]=294.2.

Workup

temperatureThe reaction mixture is again cooled to −78° C.
customReaction mixture
extractionextracted with ethyl acetate
dry with materialOrganic layer is dried over sodium sulphate, solvent
customis evaporated in vacuo
custompurified by column chromatography
washeluting 2% Ethyl acetate in hexane

Sources & evidence

ORD record: ord-a04357b2a8ec47039bf0c776e8283c48
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073894B2

Reaction notes

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