2-Tert-Butylphenol → 2-(2-Tert-butylphenoxy)-3-nitrothiophene

HRID 555429

Reaction equation

HRID 555429 reaction equation
Cl[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[N+:7]([O-:9])=[O:8].[C:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[OH:20])([CH3:13])([CH3:12])[CH3:11].C([O-])([O-])=O.[K+].[K+]>CN1C(=O)CCC1>[C:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[N+:7]([O-:9])=[O:8])([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 69232-Tert-ButylphenolHCID 11430Potassium CarbonateHCID 2201862-Chloro-3-nitrothiophene

Product 1

HCID 598573712-(2-Tert-butylphenoxy)-3-nitrothiophene

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
105 °C

Procedure

To a solution of 2-chloro-3-nitrothiophene (1.13 g, 6.93 mmol) in NMP (10 mL) in a pressure vessel was added 2-tert-butylphenol (1.04 g, 6.93 mmol) and K2CO3 (1.0 g, 10.1 mmol). The reaction was flushed with nitrogen, sealed and then heated to 105° C. for 48 h. The reaction was cooled to rt, diluted with EtOAc (˜150 mL) and washed twice with saturated aqueous NaCl (2ט150 mL). The aqueous washes were then back extracted with EtOAc. The combined organics were dried over MgSO4, filtered and concentrated to yield the crude desired product.

Workup

  1. customThe reaction was flushed with nitrogen
  2. customsealed
  3. temperatureThe reaction was cooled to rt
  4. additiondiluted with EtOAc (˜150 mL)
  5. washwashed twice with saturated aqueous NaCl (2ט150 mL)
  6. extractionThe aqueous washes were then back extracted with EtOAc
  7. dry with materialThe combined organics were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-eb9dfcffa5234e0e81072bfdd967b62b
Source dataset
uspto-grants-2011_11
Patent number
US08053450B2

Linked notes

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