Triphenylphosphine → Ethyl 12-bromododecanoate

HRID 2410623Notes

Reaction equation

HRID 2410623 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C(=O)N([Br:44])C(=O)C1>ClCCl>[Br:44][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 15635900Ethyl 12-hydroxydodecanoate

Product 1

HCID 19002561Ethyl 12-bromododecanoateYield 93.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 100 mL two-neck flask with a reflux condenser and magnetic anchor, under a static head of nitrogen, ethyl 12-hydroxydodecanoate (1.65 g, 6.7 mmol) is dissolved in dichloromethane (20 mL). PPh3 (1.93 g, 7.4 mmol) and NBS (1.6 g, 7.0 mmol) are added. The mixture is left stirring under reflux conditions for 24 hours. It is concentrated in the Rotavapor and the product is purified with column chromatography on silica gel with an eluant mixture of petroleum ether/ethyl acetate 5/1. 1.92 g (yield=92%) of ethyl 12-bromododecanoate are isolated as a light yellowish oil.

Workup

  1. waitThe mixture is left
  2. concentrationIt is concentrated in the Rotavapor
  3. customthe product is purified with column chromatography on silica gel with an eluant mixture of petroleum ether/ethyl acetate 5/1

Sources & evidence

ORD record
ord-271eb0aa7ce245d880310010a5dcac8f
Source dataset
uspto-grants-2014_08
Patent number
US08816107B2

Reaction notes

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