Water → Methyl 2-methyl-2'-(trifluoromethyl)biphenyl-4-carboxylate

HRID 219773

반응식

HRID 219773 반응식
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:12].[F:13][C:14]([F:25])([F:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].O>C1(C)C=CC=CC=1.CCOC(C)=O.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>[CH3:12][C:3]1[CH:4]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:10]=[CH:11][C:2]=1[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:14]([F:25])([F:24])[F:13]

참가 물질

8

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27343872-(Trifluoromethyl)benzeneboronic acidHCID 3294148Methyl 4-bromo-3-methylbenzoate

생성물 1

HCID 59606539Methyl 2-methyl-2'-(trifluoromethyl)biphenyl-4-carboxylate수율 96%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

Methyl 4-bromo-3-methylbenzoate (ABCR. 3 g; 13.10 mmol; 1 eq.), 2-(trifluoromethyl)phenylboronic acid (2.736 g; 14.41 mmol; 1.10 eq.), potassium carbonate (9.049 g; 65.48 mmol; 5 eq.), tetrakis(triphenylphosphine)palladium(0) (1.51 g; 1.31 mmol; 0.10 eq.) were mixed in Toluene (15 mL) and water (15 mL) under N2 atmosphere. The reaction mixture was degassed with N2 for 10 min and was heated under reflux for 3 hours. The reaction mixture was cooled to RT, filtered over a pad of celite and washed with toluene (500 mL). The filtrate was concentrated under vacuum to afford brown oil. It was taken in EtOAc (500 mL). The organic layer was washed with a saturated aqueous solution of NaHCO3 (200 mL), water (200 mL) and brine (200 mL). It was dried over MgSO4, filtered off and concentrated under vacuum giving a brown oil (3.7 g, 96%). It was used in the next step without further purification. LC/MS (Method A): 294.5 (M+H)+. HPLC (Method A) Rt 5.34 min.

후처리

  1. customThe reaction mixture was degassed with N2 for 10 min
  2. temperaturewas heated
  3. temperatureunder reflux for 3 hours
  4. filtrationfiltered over a pad of celite
  5. washwashed with toluene (500 mL)
  6. concentrationThe filtrate was concentrated under vacuum
  7. customto afford brown oil
  8. washThe organic layer was washed with a saturated aqueous solution of NaHCO3 (200 mL), water (200 mL) and brine (200 mL)
  9. dry with materialIt was dried over MgSO4
  10. filtrationfiltered off
  11. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-dd014a3b3da744b9b642a23ff1eb1ad4
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202865B2

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