Phenethyl bromide → HCID 22170046, compound

Temperature

-30 °C

To a solution of 4.6 mL of (2-bromoethyl)benzene in 70 mL ethyl ether at −70° C. was added 41.5 mL of tert-butyllithium. The mixture was slowly allowed to warm to −30° C. over 2 h, then cooled to −60° C. and treated with 5.0 g of 2,4-dichloropyrimidine The reaction was again slowly allowed to warm to −30° C. over 2 h, then quenched by the addition of 1.94 mL of acetic acid and 0.30 mL of water in 5 mL tetrahydrofuran. The mixture was treated with 7.6 g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in 25 mL THF and warmed to room temperature. The reaction was cooled to 0° C. and 13.4 mL of ice-cold 3 M NaOH was added to the mixture. After 5 minutes, the organic layer was separated and dried over sodium sulfate. The solvent was evaporated and the crude residue was chromatographed (2% to 10% EtOAc in hexanes) to give 4.0 g of 2,4-dichloro-6-phenethylpyrimidine.

1. temperaturecooled to −60° C.
2. temperatureto warm to −30° C. over 2 h
3. customquenched by the addition of 1.94 mL of acetic acid and 0.30 mL of water in 5 mL tetrahydrofuran
4. additionThe mixture was treated with 7.6 g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in 25 mL THF
5. temperaturewarmed to room temperature
6. temperatureThe reaction was cooled to 0° C.
7. addition13.4 mL of ice-cold 3 M NaOH was added to the mixture
8. customthe organic layer was separated
9. dry with materialdried over sodium sulfate
10. customThe solvent was evaporated
11. customthe crude residue was chromatographed (2% to 10% EtOAc in hexanes)

ORD record

ord-517c57ea65194831abc88875321f7f5a

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07037916B2