Water → 3-(3-Cyanophenyl)benzyl alcohol

HRID 606527Notes

Reaction equation

HRID 606527 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].C(=O)([O-])[O-].[Na+].[Na+].[OH:16][CH2:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1.O>C1(C)C=CC=CC=1.CCO.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>[OH:16][CH2:17][C:18]1[CH:23]=[C:22]([C:2]2[CH:9]=[CH:8][CH:7]=[C:4]([C:5]#[N:6])[CH:3]=2)[CH:21]=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 233813-BromobenzonitrileHCID 2734662[3-(Hydroxymethyl)phenyl]boronic acid

Product 1

HCID 13927703-(3-Cyanophenyl)benzyl alcoholYield 93%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of 3-bromobenzonitrile (1.20 g, 6.58 mmol) in toluene (40 mL) was added a solution of tetrakistriphenylphosphinepalladium (0.38 g, 0.33 mmol), 2N aqueous sodium carbonate solution (21 mL) and [3-(hydroxymethyl)phenyl]boronic acid (1.00 g, 6.58 mmol) in EtOH (19 mL), and the mixture was heated under reflux for 10 hr under nitrogen atmosphere. The reaction mixture was cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/9→1/1) to give the title compound as a yellow oil (1.28 g, 93%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 10 hr under nitrogen atmosphere
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/9→1/1)

Sources & evidence

ORD record
ord-e5e4c2741ffa45b0a2e4eee8aecdc351
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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