1-Bromooctadecane → HCID 21479728, compound
Reaction equation
C([Li])CCC.[S:6]1[CH:10]=[CH:9][C:8]2[S:11][CH:12]=[CH:13][C:7]1=2.[S].S1[C:19]([Li])=[CH:18][C:17]2[S:21][CH:22]=[CH:23][C:16]1=2.[CH2:24](Br)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]CCCCCC.[Cl-].[NH4+]>C(OCC)C>[CH2:22]([S:21][C:10]1[S:6][C:7]2[CH:13]=[CH:12][S:11][C:8]=2[CH:9]=1)[CH2:23][CH2:16][CH2:17][CH2:18][CH2:19][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH3:24]Participants
Procedure
47 ml (75 mmol) of 1.6N n-butyllithium are added dropwise at room temperature under nitrogen as blanketing gas to 10 g (71 mmol) of thieno[3,2-b]thiophene dissolved in dry diethyl ether. The mixture is then allowed to reflux for 30 minutes. Subsequently, 2.4 g (75 mmol) of dried sulfur are added with ice cooling and vigorous stirring to the resulting suspension of the thieno[3,2-b]thiophenyl lithium salt. The mixture is then allowed to warm to room temperature and stirred for 60 minutes. After renewed cooling by means of an ice bath, 23.7 g (71 mmol) of octadecyl bromide dissolved in 100 ml of dry diethyl ether are then added dropwise. After the mixture has been stirred overnight at room temperature, 50 ml of 25% ammonium chloride solution are added with ice cooling.
Workup
- temperatureto reflux for 30 minutes
- temperatureAfter renewed cooling by means of an ice bath
- additionare then added dropwise
- stirringAfter the mixture has been stirred overnight at room temperature
Sources & evidence
- ORD record
- ord-bec1e82f2075460ea03e8842cef216ba
- Source dataset
- uspto-grants-1995_07
- Patent number
- US05432286
Reaction notes
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