p-Bromochlorobenzene → (Chloromethyl)(4-chlorophenyl)dimethylsilane

HRID 2413292

반응식

HRID 2413292 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][CH:3]=1.Cl[Si:10]([CH2:13][Cl:14])([CH3:12])[CH3:11].C([Li])CCC>O1CCCC1.CCCCCC.CCOCC.[Cl-].[Li+]>[Cl:14][CH2:13][Si:10]([C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][CH:3]=1)([CH3:12])[CH3:11]

참가 물질

8

반응물 3

HCID 7806p-BromochlorobenzeneHCID 74393Silane, chloro(chloromethyl)dimethyl-HCID 178418339Butyllithium

생성물 1

HCID 2733089(Chloromethyl)(4-chlorophenyl)dimethylsilane수율 55%

시약·촉매·용매 4

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매HCID 433294Lithium Chloride용매

실험 절차

A solution of 9.6 g (0.050 mol) of 4-bromochlorobenzene and 6.6 ml (7.2 g, 0.050 mol) of chloro(chloromethyl)dimethylsilane in 75 ml of tetrahydrofuran was stirred at -78° under nitrogen while 31 ml (0.050 mol) of 1.6 molar n-butyllithium in hexane was added dropwise. The resulting clear solution was allowed to warm to room temperature, diluted with ether until no more lithium chloride precipitated, and filtered. Evaporation of the filtrate left 10.6 g of a light yellow liquid, which was distilled to give 6.0 g (55%) of the title compound as a colorless liquid: bp 54°-58° C. (0.05 mm); ir (neat) 2910, 1560, 1470, 1370, 1250, 1080, 1010, 840, 805, 790, 740 cm-1 ; nmr (CDCl3) 0.4 (6H, s), 2.9 (2H, s), 7.1-7.6 (4H, q).

후처리

  1. additionwas added dropwise
  2. customprecipitated
  3. filtrationfiltered
  4. customEvaporation of the filtrate
  5. waitleft 10.6 g of a light yellow liquid, which
  6. distillationwas distilled

출처 및 근거

ORD 기록
ord-58178a78257048aa8400632e9ceb7255
출처 데이터셋
uspto-grants-1985_01
특허 번호
US04496551

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