Water → HCID 13020231, compound

HRID 2055730Notes

Reaction equation

HRID 2055730 reaction equation
O.Br[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]#[N:11])=[CH:5][C:4]=1[F:12].C(=O)([O-])[O-].[Na+].[Na+].[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1(C)C=CC=CC=1>[F:12][C:4]1[CH:5]=[C:6]([CH2:9][C:10]#[N:11])[CH:7]=[CH:8][C:3]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 116009532-(4-Bromo-3-fluorophenyl)acetonitrile

Product 1

HCID 13020231HCID 13020231, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A biphasic mixture of water (3 mL) and toluene (10 mL) containing (4-bromo-3-fluoro-phenyl)-acetonitrile (457 mg, 2.14 mmol), sodium carbonate (1.00 g, 9.45 mmol), phenyl boronic acid (781 mg, 6.41 mmol) was sparged with nitrogen for 10 min, tetrakis(triphenylphosphine)palladium (250 mg) was added and the mixture heated to reflux for 48 hrs. After cooling, the solution was diluted with EtOAc, washed with water, the organic phase dried (MgSO4), filtered and evaporated to dryness. The residue was purified by column chromatography (0 to 10% EtOAc in hexanes) to afford (2-fluoro-biphenyl-4-yl)-acetonitrile as a colorless solid. 1H NMR (500 MHz, CDCl3) δ 7.54 (2H, m), 7.46 (3H, m), 7.40 (1H, m), 7.17 (2H, m), 3.79 (3H, s).

Workup

  1. customwas sparged with nitrogen for 10 min
  2. additiontetrakis(triphenylphosphine)palladium (250 mg) was added
  3. temperaturethe mixture heated
  4. temperatureto reflux for 48 hrs
  5. temperatureAfter cooling
  6. additionthe solution was diluted with EtOAc
  7. washwashed with water
  8. dry with materialthe organic phase dried (MgSO4)
  9. filtrationfiltered
  10. customevaporated to dryness
  11. customThe residue was purified by column chromatography (0 to 10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-7843e70ed7c94439bfd1f3efbb0b145e
Source dataset
uspto-grants-2008_02
Patent number
US07332516B2

Reaction notes

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