1-Tetracosanol → 1-Bromotetracosane
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)Br.[CH2:25](O)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47]C>ClCCl>[CH2:20]([Br:24])[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH3:25]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A series of n-alkyl bromides (CnH2n+1Br) were purchased from TCI (n=3, 6, 9, 12, 15, and 18) and Aldrich (n=22), and used as received. 1-Tetracosyl bromide (n-C24H49Br) was prepared from the corresponding alcohol (Aldrich) according to the following procedure. Triphenylphosphine (95 mg, 0.36 mmol) and carbontetrabromide (120 mg, 0.36 mmol) were sequentially introduced into a dichloromethane solution (50 ml) dissolved with 1-tetracosanol (60 mg, 0.17 mmol), and the mixture was stirred at room temperature for 12 hr. The solvent was then removed by evacuation, and the produced 1-tetracosyl bromide was isolated from the reaction mixture by column chromatography. 4-[4-(Dimethylamino)styryl]pyridin (Aldrich), tetraethylorthosilicate (TEOS, Acros), sodium aluminate (NaAlO2, Kanto) and tetrapropylammonium hydroxide (TPAOH, Aldrich) were purchased, and used as received. n-Octadecane and n-heptadecane were purchased from PolyScience Corporation and used as such. 4-Nitroaniline was purchased from Aldrich, and used as such.
Workup
- customThe solvent was then removed by evacuation
Sources & evidence
- ORD record
- ord-fa543cd35e9b429980f30ed5ba641627
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07674405B2
Reaction notes
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