Sulfuric Acid → 1-Chloro-4-(1-trimethylsilylhexyl)benzene

HRID 248567

反応式

HRID 248567 の反応式
[Mg].Br[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1.[CH3:16][Si:17]([CH3:20])([CH3:19])Cl.S(=O)(=O)(O)O>BrCCCCCCC1C=CC(Cl)=CC=1.O1CCCC1.COC(C)(C)C.[Li+].[Li+].[Cl-].[Cl-].[Cl-].[Cl-].[Cu+2]>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([CH:8]([Si:17]([CH3:20])([CH3:19])[CH3:16])[CH2:7][CH2:6][CH2:5][CH2:4][CH3:3])=[CH:10][CH:11]=1

参加物

9

反応物 4

HCID 1118Sulfuric AcidHCID 6397ChlorotrimethylsilaneHCID 5806791-(6-Bromohexyl)-4-chlorobenzeneHCID 5462224Magnesium

生成物 1

HCID 197638591-Chloro-4-(1-trimethylsilylhexyl)benzene収率 39%

試薬・触媒・溶媒 4

HCID 193501Copper;dilithium;tetrachloride触媒HCID 5806791-(6-Bromohexyl)-4-chlorobenzene触媒HCID 8028Tetrahydrofuran溶媒3 回HCID 15413tert-Butyl methyl ether溶媒

反応条件

温度
60 °C

実験手順

Approximately 2 g (82 mMol) of magnesium in a flask were moistened with tetrahydrofuran. A Grignard reaction was initiated using 5 drops of 1-(6-bromohexyl)-4-chlorobenzene. The remainder of a total of 17 g of the halogen compound (61 mMol), dissolved in 50 ml of tetrahydrofuran, was added dropwise at 50° to 60° C. When the addition was complete, the mixture was kept at this temperature for an additional 2.5 hours, and a solution of 12 g (110 mMol) of trimethylchlorosilane and a catalytic amount of dilithium tetrachlorocuprate in 40 ml of tetrahydrofuran was then added dropwise at 20° to 40° C. The mixture was stirred at 60° C. for 1 hour, then allowed to stand overnight and diluted with 200 ml of tert-butyl methyl ether. The mixture was then acidified using 2N sulfuric acid, the phases were separated, and the organic phase was washed and dried. The evaporated residue was fractionated. About 6.4 g of 1-chloro-4-(1-trimethylsilylhexyl)benzene (38.6 percent yield) were obtained at a pressure of 0.2 hPa and at 88° to 90° C.

後処理

  1. customA Grignard reaction
  2. additionwas added dropwise at 50° to 60° C
  3. additionWhen the addition
  4. waitto stand overnight
  5. customthe phases were separated
  6. washthe organic phase was washed
  7. customdried

出典と根拠

ORDレコード
ord-199d6f6eb60e456080d3e5aa1cc42175
出典データセット
uspto-grants-1993_05
特許番号
US05210247

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