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Ethanol → 5'-Isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-carbonitrile

HRID 17047
Notes
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Reaction equation

HRID 17047 reaction equation
I[C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[C:4]#[N:5].[CH:14]([C:17]1[CH:18]=[CH:19][C:20]([O:26][CH3:27])=[C:21](B(O)O)[CH:22]=1)([CH3:16])[CH3:15].C([O-])([O-])=O.[Na+].[Na+].C(O)C>CC(O)C(O)C.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.O>[CH:14]([C:17]1[CH:18]=[CH:19][C:20]([O:26][CH3:27])=[C:21]([C:2]2[C:3]([C:4]#[N:5])=[CH:6][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:8][CH:9]=2)[CH:22]=1)([CH3:16])[CH3:15]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 45891905-Isopropyl-2-methoxyphenylboronic acidHCID 533636442-Iodo-5-(trifluoromethyl)benzonitrile

Product 1

HCID 533636455'-Isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-carbonitrile

Reagents, catalysts & solvents 3

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 2622,3-ButanediolSolvent
HCID 962WaterSolvent

Procedure

To a solution of 2-iodo-5-(trifluoromethyl)benzonitrile (2.0 g, 6.7 mmol) and (5-isopropyl-2-methoxyphenyl)boronic acid (1.6 g, 8.4 mmol) in dimethyl ethylene glycol (30.4 mL) was added 2M Na2CO3 (6.8 mL), ethanol (9.6 mL), and water (10 mL). The solution was degassed with nitrogen for 2 minutes. Pd(PPh3)4 (774 mg, 0.67 mmol) was added and the solution was degassed with nitrogen again for 2 minutes. The solution was divided equally into two 40 mL microwave tubes. Each tube was degassed with nitrogen for 1 minute, sealed, and placed in a microwave reactor. The wattage was set for 200 W until the temperature reached 150° C. and then the temperature was held at 150° C. for ten minutes. The tubes were then cooled to room temperature, combined, poured into H2O (50 mL), and extracted with EtOAc (100 mL). The organic layer was washed with brine (50 mL), dried over Na2SO4, filtered, and concentrated. Purification by flash chromatography with 15% CH2Cl2/hexanes afforded 5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-carbonitrile as a light yellow oil. Rf=0.65 (25% EtOAc/hexanes). 1H NMR (CDCl3, 500 MHz) δ 7.97 (s, 1H), 7.85 (d, J=8.0 Hz, 1H), 7.63 (d, J=8.0 Hz, 1H), 7.31 (dd, J=8.5, 2.0 Hz, 1H), 7.12 (d, J=2.0 Hz, 1H), 6.97 (d, J=8.5 Hz, 1H), 3.82 (s, 3H), 2.93 (m, 1H), 1.27 (d, J=7.0 Hz, 6H).

Workup

  1. customThe solution was degassed with nitrogen for 2 minutes
  2. customthe solution was degassed with nitrogen again for 2 minutes
  3. customEach tube was degassed with nitrogen for 1 minute
  4. customsealed
  5. customplaced in a microwave reactor
  6. customreached 150° C.
  7. waitthe temperature was held at 150° C. for ten minutes
  8. additionpoured into H2O (50 mL)
  9. extractionextracted with EtOAc (100 mL)
  10. washThe organic layer was washed with brine (50 mL)
  11. dry with materialdried over Na2SO4
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customPurification by flash chromatography with 15% CH2Cl2/hexanes

Sources & evidence

ORD record
ord-6e0179bcbd774ab6b97e9ae447118345
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07737295B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes