Pyridine → 157581-03-8

HRID 1494520Notes

Reaction equation

[C:1]([C:5]1[CH:13]=[CH:12][C:8]([CH:9](O)[CH3:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.P(Br)(Br)[Br:21]>C(OCC)C>[C:1]([C:5]1[CH:13]=[CH:12][C:8]([CH:9]([Br:21])[CH3:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -10 °C

Procedure

To 25 ml of ethyl ether were added 1.78 g of (+)-4-tert.-butyl-α-methylbenzyl alcohol of 100% e.e. and 1.8 g of dry pyridine. The resulting mixed solution was kept at -25° C. and added dropwise with a solution of 3.1 g of phosphorus tribromide dissolved in 18 ml of ethyl ether (at -15° to -25° C.). After completion of addition, the resulting mixture was stirred at -10° C. for one hour and then allowed to stand at 5° C. for 2 days. Ice water was added thereto. The resulting organic layer was washed successively with a saturated aqueous solution of sodium bicarbonate and with ice water, dried with anhydrous Glauber's salt, and freed of solvent by distillation under reduced pressure to give 1.6 g of 4-tert.-butyl-α-methylbenzyl bromide.

Workup

additionThe resulting mixed solution
customwas kept at -25° C.
additionAfter completion of addition
waitto stand at 5° C. for 2 days
washThe resulting organic layer was washed successively with a saturated aqueous solution of sodium bicarbonate and with ice water
dry with materialdried with anhydrous Glauber's salt
distillationfreed of solvent by distillation under reduced pressure

Sources & evidence

ORD record: ord-f638db8bd3ce41bb8850fdc4dd7aa6c0
Source dataset: uspto-grants-1991_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05026850

Reaction notes

Loading…