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Chlorodiphenylphosphine → HCID 20039974, 화합물

HRID 1762904
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인쇄 미리보기

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HRID 1762904 반응식
Br[C:2]1[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:5]([O:6][Si:7]([CH3:10])([CH3:9])[CH3:8])=[C:4]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH:3]=1.C([Li])CCC.[C:26]1([P:32]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)Cl)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[Cl-].[Li+]>O1CCCC1.CCCCCC>[C:17]([C:4]1[CH:3]=[C:2]([P:32]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:5]=1[O:6][Si:7]([CH3:10])([CH3:9])[CH3:8])([CH3:20])([CH3:19])[CH3:18]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 66180ChlorodiphenylphosphineHCID 433294Lithium ChlorideHCID 10882840(2,6-Di-tert-butyl-4-bromophenoxy)trimethylsilaneHCID 178418339Butyllithium

생성물 1

HCID 20039974HCID 20039974, 화합물수율 107.3%

시약·촉매·용매 2

HCID 8028
Tetrahydrofuran
용매
HCID 8058Hexane용매

반응 조건

온도
-78 °C

실험 절차

A stirred suspension of 20.0 g (56 mmol) of 4-bromo-2,6-di-tert-butylphenoxy(trimethyl)silane in 80 ml of dry tetrahydrofuran at -78° C. is admixed dropwise with 38 ml (56 mmol) of a 1.55M solution of n-butyllithium in hexane. The resulting homogeneous solution is stirred for 1 hour at -78° C. and then 12.36 g (56 mmol) of diphenylchlorophosphine is added dropwise. The reaction mixture is stirred for 24 hours at room temperature, and then the suspension of lithium chloride is removed by filtration. The solvent is removed in vacuo. The residue is dissolved in 250 ml of diethyl ether and extracted (3×250 ml) with water. The organic phase is dried over anhydrous sodium sulfate and evaporated in vacuo to give 27.8 grams of a yellow liquid. The crude product is purified by preparative HPLC (silica gel, 99:1 heptane:ethyl acetate eluent) to give 10.7 grams (41%) of a white solid, m.p. 76°-80° C.

후처리

  1. stirringThe reaction mixture is stirred for 24 hours at room temperature
  2. customis removed by filtration
  3. customThe solvent is removed in vacuo
  4. dissolutionThe residue is dissolved in 250 ml of diethyl ether
  5. extractionextracted (3×250 ml) with water
  6. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  7. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-7f7e08b7485648e2823c02130fa42f63
출처 데이터셋
uspto-grants-1989_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04835202

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