Benzenemethanol, 4-chloro-alpha-methyl- → 1-(1-Bromoethyl)-4-chlorobenzene

HRID 1444617Notes

Reaction equation

HRID 1444617 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[CH3:9])=[CH:4][CH:3]=1.P(Br)(Br)[Br:12].C(=O)([O-])O.[Na+]>C(OCC)C>[Br:12][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH3:9]

Participants

5

Reactant 3

HCID 18825Benzenemethanol, 4-chloro-alpha-methyl-HCID 24614Phosphorus tribromideHCID 516892Sodium Bicarbonate

Product 1

HCID 857721-(1-Bromoethyl)-4-chlorobenzeneYield 82%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of the above product 1-(4-chlorophenyl)ethanol in 100 ml of diethyl ether was slowly added a solution of 13.5 g (50 mmoles) of phosphorus tribromide in 50 ml of diethyl ether. The resulting solution was stirred overnight at room temperature. The reaction mixture was poured into ice water. Sodium hydrogencarbonate was added to the resulting solution for neutralization, and the organic layer was extracted with diethyl ether. The organic layer was collected, washed with water, dried over anhydrous sodium sulfate and concentrated in a vacuum, giving 9.00 g (41 mmoles, 82% in yield) of 1-(1-bromoethyl)-4-chlorobenzene [1H-NMR (300 MHz, CDCl3) 2.02 (d, J=6.9 Hz, 3H), 5.1 (q, J=6.9 Hz, 1H), 7.26-7.40 (m, 4H)] in a nearly pure form.

Workup

  1. extractionthe organic layer was extracted with diethyl ether
  2. customThe organic layer was collected
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in a vacuum

Sources & evidence

ORD record
ord-f3577db30e0a49c9b14ab1ee40a031f7
Source dataset
uspto-grants-2010_02
Patent number
US07662899B2

Reaction notes

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