Sodium Carbonate → 3-[2-(Benzyloxy)-5-chlorobenzyl]benzonitrile

HRID 1945222Notes

Reaction equation

HRID 1945222 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1B(O)O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24]Br)#[N:20].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[CH2:24][C:23]1[CH:22]=[C:21]([CH:28]=[CH:27][CH:26]=1)[C:19]#[N:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 97249Benzonitrile, 3-(bromomethyl)-HCID 41987402-Benzyloxy-5-chlorobenzeneboronic acid

Product 1

HCID 669961093-[2-(Benzyloxy)-5-chlorobenzyl]benzonitrile

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-benzyloxy-5-chlorophenylboronic acid (2.1 g), 3-cyanobenzyl bromide (1.57 g), sodium carbonate (1.7 g) and tetrakis(triphenylphosphine)palladium (0) (0.46 g) in ethylene glycol dimethyl ether (30 ml) was heated at 80° C. for 5 h. The mixture was cooled, partitioned between water/diethylether, the organics separated, dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 5% ethylacetate/isohexane, yield 0.53 g.

Workup

  1. temperatureThe mixture was cooled
  2. custompartitioned between water/diethylether
  3. customthe organics separated, dried
  4. customevaporated under reduced pressure
  5. customThe residue was purified by chromatography on silica eluting with 5% ethylacetate/isohexane, yield 0.53 g

Sources & evidence

ORD record
ord-ebb5c169d374417a8e027864cf48bc4b
Source dataset
uspto-grants-2013_03
Patent number
US08394986B2

Reaction notes

Loading…