Triphenylphosphine → 1-(2-Bromoethyl)-4-chlorobenzene

HRID 467056Notes

Reaction equation

HRID 467056 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7]O)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:30]N1C(=O)CCC1=O>C1COCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][Br:30])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 74647p-Chlorophenethylic alcohol

Product 1

HCID 230291-(2-Bromoethyl)-4-chlorobenzeneYield 54.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred solution of 4-chlorophenethyl alcohol (131 g) and triphenylphosphine (241.3 g) in dry THF (500 mL) at 0° C. was treated portionwise over 30 min. with N-bromosuccinimide (163.75 g). The resulting black solution was stirred overnight at room temperature, whereupon the THF was evaporated and the residue stirred with ether. The solution was filtered to remove triphenylphosphine oxide and the filtrate evaporated and treated with hexane. The stirred mixture was filtered, evaporated, and the residue distilled under reduced pressure to give 100 g of 4-chlorophenethyl bromide as a colorless liquid, b.p. 85° C. (3 mm Hg).

Workup

  1. customwas evaporated
  2. filtrationThe solution was filtered
  3. customto remove triphenylphosphine oxide
  4. customthe filtrate evaporated
  5. additiontreated with hexane
  6. filtrationThe stirred mixture was filtered
  7. customevaporated
  8. distillationthe residue distilled under reduced pressure

Sources & evidence

ORD record
ord-2e4d1e7cdffd4ebcab50d5c29480665a
Source dataset
uspto-grants-1992_10
Patent number
US05158949

Reaction notes

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