Hexane → 1-Bromo-4-[4-(methoxymethylidene)cyclohexyl]benzene

HRID 1975614Notes

Reaction equation

HRID 1975614 reaction equation
[Cl-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:9][O:10][CH3:11])C=CC=CC=1.[Br:24][C:25]1[CH:30]=[CH:29][C:28]([CH:31]2[CH2:36][CH2:35][C:34](=O)[CH2:33][CH2:32]2)=[CH:27][CH:26]=1.CCCCCC>COC(C)(C)C.O1CCCC1>[Br:24][C:25]1[CH:30]=[CH:29][C:28]([CH:31]2[CH2:36][CH2:35][C:34](=[CH:9][O:10][CH3:11])[CH2:33][CH2:32]2)=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 8058HexaneHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 100835924-(4-BROMOPHENYL)CYCLOHEXANONE

Product 1

HCID 190979141-Bromo-4-[4-(methoxymethylidene)cyclohexyl]benzeneYield 93.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

20.4 g of triphenyl-methoxymethyl-phosphonium chloride were suspended in 60 ml of t-butyl methyl ether while gassing with argon in a sulphonation flask having a thermometer, mechanical stirrer, dropping funnel and solid substance addition tube and treated at -10° C. within 10 minutes with 6.6 g of solid potassium t-butylate. After completion of the addition the mixture was stirred at -10° C. to 0° C. for 30 minutes, then the deep orange, heterogeneous reaction mixture was treated dropwise at 0° C. with a solution of 10 g of 4-(4-bromophenyl)cyclohexanone in 50 ml of absolute tetrahydrofuran, subsequently stirred at room temperature for 24 hours, poured into 500 ml of hexane and filtered. Low-pressure chromatography of the concentrated residue (13.9 g) on silica gel with hexane/ethyl acetate (vol. 9:1) gave 10.4 g of 1-bromo-4-[4-(methoxymethylidene)cyclohexyl]benzene as a colourless oil.

Workup

  1. customwhile gassing with argon in a sulphonation flask
  2. additionfunnel and solid substance addition tube
  3. additionAfter completion of the addition the mixture
  4. stirringsubsequently stirred at room temperature for 24 hours
  5. filtrationfiltered

Sources & evidence

ORD record
ord-c7d89244b33a41298f701f20d983df87
Source dataset
uspto-grants-1994_02
Patent number
US05288428

Reaction notes

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