p-Bromochlorobenzene → HCID 12501054, compound
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5](Cl)=CC=1.[Cl:9][CH2:10][SiH2:11][CH:12](Cl)Cl.[CH2:15]([Li])[CH2:16][CH2:17][CH3:18]>O1CCCC1.CCCCCC.[Cl-].[Li+]>[Cl:9][CH2:10][Si:11]([CH2:2][CH2:7][CH2:6][CH3:5])([CH2:15][CH2:16][CH2:17][CH3:18])[CH3:12]Participants
Procedure
A solution of 14.4 g (0.075 mol) of 4-bromochlorobenzene and 9.5 ml (12.3 g, 0.075 mol) of chloromethyl(dichloro)methylsilane in 150 ml of tetrahydrofuran was cooled to -60° under nitrogen and stirred while 94 ml (0.15 mol) of 1.6 molar n-butyllithium in hexane was added dropwise at a rate that held the mixture between -65° and -55°. The resulting slurry was allowed to warm to room temperature, giving a solution that was diluted with hexanes until no more lithium chloride precipitated. Filtration, evaporation of the filtrate, dissolution of the residue in hexanes, refiltration, and evaporation left 19.8 g of a pale orange liquid. Distillation gave first 1.8 g (12%) of chloromethyl(dibutyl)methylsilane, bp 45° C. (0.05 mm), followed by 6.8 g (35%) of the title compound as a colorless liquid: bp 90° C. (0.05 mm); nD21 1.5246; ir (neat) 2925, 1580, 1380, 1260, 1090, 1015, 820, 740 cm-1 ; nmr (CDCl3) 0.4 (3H, s), 0.6-1.5 (9H, m), 2.9 (2H, s), 7.0-7.4 (4H, q).
Workup
- additionwas added dropwise at a rate that
- customthe mixture between -65° and -55°
- customgiving a solution that
- customprecipitated
- filtrationFiltration, evaporation of the filtrate, dissolution of the residue in hexanes
- customrefiltration, and evaporation
- waitleft 19.8 g of a pale orange liquid
- distillationDistillation
Sources & evidence
- ORD record
- ord-c0d1f7c977d54dd5aaf8e935780b717c
- Source dataset
- uspto-grants-1985_04
- Patent number
- US04510136
Reaction notes
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