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

HRID 1980502

反応式

HRID 1980502 の反応式
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]

参加物

8

反応物 3

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

生成物 1

HCID 2733089(Chloromethyl)(4-chlorophenyl)dimethylsilane収率 55%

試薬・触媒・溶媒 4

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒HCID 433294Lithium Chloride溶媒

実験手順

A solution of 9.6 g (0.050 mol) of 4-bromochlorobenzene and 6.6 ml (7.2 g, 0.050 mol) of chlorochloromethyldimethylsilane 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).

後処理

  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

出典と根拠

ORDレコード
ord-31f44f32b71a4cc8a21c2ae6682da9d5
出典データセット
uspto-grants-1985_04
特許番号
US04510136

関連ノート

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