Triethylamine → [4-fluoro-2-[(E)-2-(4-fluorophenyl)ethenyl]phenyl]methanol

HRID 878645Notes

Reaction equation

HRID 878645 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][OH:10].[F:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]=[CH2:19])=[CH:14][CH:13]=1.CCN(CC)CC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C=O)C>[F:8][C:6]1[CH:5]=[CH:4][C:3]([CH2:9][OH:10])=[C:2](/[CH:19]=[CH:18]/[C:15]2[CH:16]=[CH:17][C:12]([F:11])=[CH:13][CH:14]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 678834-FluorostyreneHCID 2773347(2-Bromo-4-fluorophenyl)methanol

Product 1

HCID 86725608[4-fluoro-2-[(E)-2-(4-fluorophenyl)ethenyl]phenyl]methanolYield 50%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

Charged (2-bromo-4-fluorophenyl)methanol (954 mg, 4.65 mmol), 4-fluoro-1-vinylbenzene (1.14 g, 9.31 mmol), Pd(PPh3)2Cl2(49 mg, 0.07 mmol), Et3N (942 mg, 9.31 mmol) and DMF (5 mL) to a sealed tube, the mixture was then purged with nitrogen, heated to 150° C. for 3 h in microwave oven. The reaction mixture was filtered, the filtrate was then extracted with ethyl acetate, concentrated and purified by flash column chromatograph to give 569 mg of the title compound (50%). 1H NMR (400 MHz, CDCl3): δ 1.60 (1H, t, J=6.4 Hz), 4.78 (2H, d, J=6.4 Hz), 6.93-7.08 (4H, m), 7.31-7.35 (3H, m), 7.48-7.52 (2H, m).

Workup

  1. customthe mixture was then purged with nitrogen
  2. filtrationThe reaction mixture was filtered
  3. extractionthe filtrate was then extracted with ethyl acetate
  4. concentrationconcentrated
  5. custompurified by flash column chromatograph

Sources & evidence

ORD record
ord-8b445d36b0c54086aba6b4d9bd747b87
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Reaction notes

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