Chlorodiphenylphosphine → HCID 20039974, compound

HRID 1762904Notes

Reaction equation

HRID 1762904 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

HCID 20039974HCID 20039974, compoundYield 107.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7f7e08b7485648e2823c02130fa42f63
Source dataset
uspto-grants-1989_05
Patent number
US04835202

Reaction notes

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