Cesium carbonate → (4'-(Trifluoromethyl)-[1,1'-biphenyl]-4-yl)methanol

HRID 1296048Notes

Reaction equation

HRID 1296048 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[OH:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CN(C=O)C.C1COCC1>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([C:17]2[CH:18]=[CH:19][C:14]([CH2:13][OH:12])=[CH:15][CH:16]=2)=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 27347064-(Hydroxymethyl)benzeneboronic acid

Product 1

HCID 22015014(4'-(Trifluoromethyl)-[1,1'-biphenyl]-4-yl)methanol

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

1-Bromo-4-trifluoromethyl-benzene (814 mg, 3.62 mmol), 4-hydroxymethylphenylboronic acid (600 mg, 3.98 mmol), cesium carbonate (2.36 g, 7.24 mmol), and PdCl2(dppf) (132 mg, 0.181 mmol) were added to 10 ml of a 1:1 solution of DMF/THF. The reaction was flushed with nitrogen and heated to 90° C. for 1 h. The reaction was cooled, poured into diethyl ether and washed with water (2×50 ml), brine (1×50 ml) and dried over anhydrous sodium sulfate. The crude product was filtered through silica gel, eluted with diethyl ether, and concentrated to provide the title compound. MS m/z 251 (M−1).

Workup

  1. customThe reaction was flushed with nitrogen
  2. temperatureThe reaction was cooled
  3. additionpoured into diethyl ether
  4. washwashed with water (2×50 ml), brine (1×50 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe crude product was filtered through silica gel
  7. washeluted with diethyl ether
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-36d325af8b324f31aa9e3985fe9965a6
Source dataset
uspto-grants-2007_07
Patent number
US07244763B2

Reaction notes

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