Water → HCID 19019128, compound

HRID 1168546Notes

Reaction equation

HRID 1168546 reaction equation
[Cl:1][C:2]1[C:3]([CH:16](O)[CH3:17])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.P(Br)(Br)[Br:20].O.[C:24]1([P:30]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CCOCC.CCCCCC>[Br-:20].[Cl:1][C:2]1[C:3]([CH2:16][CH2:17][P+:30]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 24614Phosphorus tribromideHCID 22992384HCID 22992384, compound

Product 1

HCID 19019128HCID 19019128, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

To a solution of 3.15 g (11.8 mmol) of (±)-1-(3-chloro-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl)ethanol in ether and hexane stirring at 0° C. under argon, was added dropwise 31.9 g (11.2 mL, 118 mmol) of phosphorus tribromide and the mixture stirred 1.5 hours. Water was then carefully added and the mixture extracted with several portions of ether. The ether extracts were washed with water, sodium bicarbonate, brine, and dried (MgSO4). The solvent was removed in-vacuo and the residual oil taken up in 175 mL of benzene. To this was added 3.09 g (11.8 mmol) of triphenylphosphine and the solution stirred for 24 hours at room temperature. Purification was done using flash chromatography (SiO2, 0.5% ethyl acetate in hexanes, 5% MeOH in methylene chloride) to give the title compound as a white foam.

Workup

  1. extractionthe mixture extracted with several portions of ether
  2. washThe ether extracts were washed with water, sodium bicarbonate, brine
  3. dry with materialdried (MgSO4)
  4. customThe solvent was removed in-vacuo
  5. stirringthe solution stirred for 24 hours at room temperature
  6. customPurification

Sources & evidence

ORD record
ord-0a37a39fdce54cc4a5620fbbc121fa6a
Source dataset
uspto-grants-2003_09
Patent number
US06624188B1

Reaction notes

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