Phosphine, triphenyl-, hydrobromide → [1-(4,5,6,7-Tetrahydro-4,4,7,7-tetramethylbenzo-[b]thien-2-yl)ethyl]triphenylphosphonium bromide

HRID 485033Notes

Reaction equation

HRID 485033 reaction equation
[CH3:1][CH:2]([C:4]1[S:8][C:7]2[C:9]([CH3:16])([CH3:15])[CH2:10][CH2:11][C:12]([CH3:14])([CH3:13])[C:6]=2[CH:5]=1)O.[Br-:17].[C:18]1([PH+:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(#N)C>[Br-:17].[CH3:13][C:12]1([CH3:14])[C:6]2[CH:5]=[C:4]([CH:2]([P+:24]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH3:1])[S:8][C:7]=2[C:9]([CH3:16])([CH3:15])[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 517696Phosphine, triphenyl-, hydrobromideHCID 867402444,5,6,7-Tetrahydro-alpha,4,4,7,7-pentamethylbenzo[b]thiophene-methanol

Product 1

HCID 23049224[1-(4,5,6,7-Tetrahydro-4,4,7,7-tetramethylbenzo-[b]thien-2-yl)ethyl]triphenylphosphonium bromideYield 103.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

20.2 g of 4,5,6,7-tetrahydro-α,4,4,7,7-pentamethylbenzo[b]thiophene-methanol are dissolved in 260 ml of acetonitrile and the solution is treated with 29.2 g of triphenylphosphonium bromide. After stirring at 50° C. for 3 hours, the mixture is evaporated to dryness, the residue is taken up with 80% aqueous ethanol and extracted twice with hexane. The ethanol phase is evaporated, the residue is dissolved in methylene chloride, the solution is dried over sodium sulphate and evaporated. There are obtained 49.4 g of [1-(4,5,6,7-tetrahydro-4,4,7,7-tetramethylbenzo[b]thien-2-yl)ethyl]triphenylphosphonium bromide as an amorphous white powder.

Workup

  1. customthe mixture is evaporated to dryness
  2. extractionextracted twice with hexane
  3. customThe ethanol phase is evaporated
  4. dissolutionthe residue is dissolved in methylene chloride
  5. dry with materialthe solution is dried over sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-69dec69f8b2b4990a4d0259e37ffed11
Source dataset
uspto-grants-1985_08
Patent number
US04535086

Reaction notes

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