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

HRID 219773

反応式

HRID 219773 の反応式
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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-dd014a3b3da744b9b642a23ff1eb1ad4
出典データセット
uspto-grants-2012_06
特許番号
US08202865B2

関連ノート

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