1-Butanol → 59090-57-2

HRID 1916017Notes

Reaction equation

HRID 1916017 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:14]1([SH:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CC(C)([O-])C.[Na+].C(O)CCC>ClCCl.C(=O)([O-])O.[Na+].CCCCCC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:14]1([S:20][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:4][CH:3]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

9

Reactant 4

HCID 2631-ButanolHCID 71014-BromobiphenylHCID 7969ThiophenolHCID 23676156Sodium t-butoxide

Product 1

HCID 438715959090-57-2Yield 84%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
25 °C

Procedure

Uniformly mixed were 3.0 parts of 4-bromobiphenyl, 1.7 parts of thiophenol, 2.5 parts of sodium tert-butoxide, 0.15 parts of tetrakis(triphenylphosphine)palladium, and 64.3 parts of 1-butanol, and allowed to react at 120° C. for 2 hours. The reaction solution was cooled to room temperature (about 25° C.) and then filtered. The filtrate was transferred to a rotary evaporator, and the solvent was removed by distillation, so that a red-brown, crystalline product was obtained. The product was dissolved in 70 parts of dichloromethane, and 50 parts of an aqueous saturated sodium hydrogen carbonate solution was added thereto. After washing three times by liquid-liquid separation, the dichloromethane layer was washed with 70 parts of distilled water until the pH became neutral. The dichloromethane layer was transferred to a rotary evaporator, and the solvent was removed by distillation, so that a brown, crystalline product was obtained. Twenty parts of hexane was added thereto, and the product was dispersed in hexane using an ultrasonic cleaner. The operation of standing for about 15 minutes and then removing the supernatant was repeated three times to wash the resulting solid, and the solvent was removed with a rotary evaporator, so that brown crystalline 4-(phenylthio)biphenyl was obtained in a yield of 84%. The product was identified by 1H-NMR {d6-dimethylsulfoxide, δ (ppm) 7.6-7.7 (4H, m), 7.3-7.5 (10H, m)}.

Workup

  1. additionUniformly mixed
  2. customto react at 120° C. for 2 hours
  3. filtrationfiltered
  4. customThe filtrate was transferred to a rotary evaporator
  5. customthe solvent was removed by distillation
  6. customso that a red-brown, crystalline product was obtained
  7. additionwas added
  8. washAfter washing three times
  9. customby liquid-liquid separation
  10. washthe dichloromethane layer was washed with 70 parts of distilled water until the pH
  11. customThe dichloromethane layer was transferred to a rotary evaporator
  12. customthe solvent was removed by distillation
  13. customso that a brown, crystalline product was obtained
  14. customremoving the supernatant
  15. washto wash the resulting solid
  16. customthe solvent was removed with a rotary evaporator, so that brown crystalline 4-(phenylthio)biphenyl
  17. customwas obtained in a yield of 84%

Sources & evidence

ORD record
ord-bc7e9947d6cc40e4b9f3e321aa441862
Source dataset
uspto-grants-2013_12
Patent number
US08617787B2

Reaction notes

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