Triphenylphosphine → HCID 19083614, compound

HRID 962355Notes

Reaction equation

HRID 962355 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH:9]1([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]O)[CH2:13][CH2:12][CH2:11][CH2:10]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:1][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 19083491Cyclopentane-octanol

Product 1

HCID 19083614HCID 19083614, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.4 g of N-bromosuccinimide were added portionwise to a solution of 2.27 g of cyclopentane-octanol and 3.22 g of triphenylphosphine in 40 ml of dichloromethane in an ice bath. The reaction mixture was left to stand at room temperature overnight, filtered and the filtrate was concentrated. The residue was partitioned between 50 ml of methanol/water (vol.) 4:1 and 40 ml of hexane and the methanol phase was separated. The hexane phase was washed twice with 20 ml of methanol/water 4:1 each time and concentrated. Distillation of the residue in a bulb-tube at 130°-150° C./0.05 Torr gave 2.3 g of (8-bromooctyl)-cyclopentane as a colorless oil.

Workup

  1. waitThe reaction mixture was left
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated
  4. customThe residue was partitioned between 50 ml of methanol/water (vol.) 4:1 and 40 ml of hexane
  5. customthe methanol phase was separated
  6. washThe hexane phase was washed twice with 20 ml of methanol/water 4:1 each time
  7. concentrationconcentrated
  8. distillationDistillation of the residue in a bulb-tube at 130°-150° C./0.05 Torr

Sources & evidence

ORD record
ord-db56359c7bc5470a928e42ca6310751e
Source dataset
uspto-grants-1998_06
Patent number
US05759443

Reaction notes

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