Phosphonium, (bromomethyl)triphenyl-, bromide (1:1) → HCID 86683114, compound

Temperature

-75 °C

To a suspension of (bromomethyl)triphenylphosphonium bromide (3.06 g, 7.01 mmol) in 30 mL of THF, potassium tert-butoxide (0.78 g, 7.01 mmol) was added portionwise at −75° C. under argon. After completion of the addition, the mixture was stirred for 1 h a −75° C. Then, a solution of 3-methylquinoline-2-carbaldehyde (1 g, 5.84 mmol) in 20 mL of THF was added. The reaction mixture was stirred for 5 h at −75° C. and then allowed to warm up to room temperature overnight. For work-up, the reaction mixture was diluted with diisopropyl ether (1:1) and the precipitate formed was sucked off. The filtrate was concentrated and triturated in diisopropyl ether. The precipitate was sucked off. The filtrate was purified by column chromatography (normal phase, eluent: cyclohexane/EA) to give 492.5 mg (34%) of the title compound as yellow solid. LC-MS: m/e 248.0 (M+H)+; Rt 1.561 min.

1. additionwas added portionwise at −75° C. under argon
2. additionAfter completion of the addition
3. stirringThe reaction mixture was stirred for 5 h at −75° C.
4. temperatureto warm up to room temperature overnight
5. customthe precipitate formed
6. concentrationThe filtrate was concentrated
7. customtriturated in diisopropyl ether
8. customThe filtrate was purified by column chromatography (normal phase, eluent: cyclohexane/EA)

ORD record

ord-38e962eaa58645c38ec34740b37ceaf0

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09273068B2