Pyridine → 157581-03-8

HRID 2352520Notes

Reaction equation

HRID 2352520 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

5

Reactant 3

HCID 1049PyridineHCID 24614Phosphorus tribromideHCID 2607311-(4-tert-Butylphenyl)ethanol

Product 1

HCID 11521571157581-03-8Yield 66.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-10 °C

Procedure

To 25 ml of ethyl 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

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

Sources & evidence

ORD record
ord-861897299d504dee85fa48a3095a1007
Source dataset
uspto-grants-1989_10
Patent number
US04877787

Reaction notes

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