Pyridine → Pentafluorobenzyl bromide

HRID 414292

Reaction equation

HRID 414292 reaction equation
P(Br)(Br)[Br:2].[F:5][C:6]1[C:13]([F:14])=[C:12]([F:15])[C:11]([F:16])=[C:10]([F:17])[C:7]=1[CH2:8]O.N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[F:5][C:6]1[C:13]([F:14])=[C:12]([F:15])[C:11]([F:16])=[C:10]([F:17])[C:7]=1[CH2:8][Br:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 99232,3,4,5,6-Pentafluorobenzyl AlcoholHCID 24614Phosphorus tribromideHCID 516892Sodium Bicarbonate

Product 1

HCID 74484Pentafluorobenzyl bromide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of phosphorus tribromide (2.1 g) and toluene (1 cm3) was added dropwise to a solution of 2,3,4,5,6-pentafluorobenzylalcohol (3.4 g) and pyridine (0.21 g) in toluene (10 cm3) at 0° C. The reaction mixture was stirred at 0° C. for 45 minutes, then at the ambient temperature (ca. 20° C.) for 75 minutes, and was then added to an excess of saturated sodium bicarbonate solution. The products were extracted into diethyl ether, and the combined ether layers dried and concentrated by evaporation under reduced pressure. The residual solution (still containing toluene) was passed through a plug of silica gel.

Workup

  1. waitat the ambient temperature (ca. 20° C.) for 75 minutes
  2. extractionThe products were extracted into diethyl ether
  3. dry with materialthe combined ether layers dried
  4. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-fb35ab862083431995ce10c40a743973
Source dataset
uspto-grants-1988_12
Patent number
US04791139

Linked notes

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