Sodium Carbonate → HCID 20099829, compound

HRID 1867542Notes

Reaction equation

HRID 1867542 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.[F:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27914Benzeneacetonitrile, 4-bromo-HCID 2856454-Fluorophenylboronic acid

Product 1

HCID 20099829HCID 20099829, compound

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

The method described in Example 3 (step 3.2.) is used. Starting from 4.12 g (32.48 mmol) of (4-bromophenyl)acetonitrile, 5 g (35.73 mmol) of 4-fluorophenylboronic acid, 32.48 ml (64.96 mmol) of aqueous sodium carbonate (2M) solution and 1.24 g (1.07 mmol) of palladium tetrakis(triphenylphosphine), 3.3 g of pure product are obtained in the form of a white solid, following chromatography on silica gel, eluting with a 15/85 mixture of ethyl acetate and cyclohexane.

Workup

  1. customare obtained in the form of a white solid
  2. washeluting with a 15/85 mixture of ethyl acetate and cyclohexane

Sources & evidence

ORD record
ord-4ceedbcb3fa948a295eadbed357fee13
Source dataset
uspto-grants-2009_12
Patent number
US07632850B2

Reaction notes

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