4-Hydroxybiphenyl → HCID 39158632, compound

HRID 1361014Notes

Reaction equation

HRID 1361014 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[C:16]([C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH2:21]Br)#[N:17]>CN(C)C=O>[C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:8]=[CH:9][C:10]([O:13][CH2:21][C:20]2[CH:19]=[C:18]([CH:25]=[CH:24][CH:23]=2)[C:16]#[N:17])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 71034-HydroxybiphenylHCID 24758Sodium hydrideHCID 97249Benzonitrile, 3-(bromomethyl)-

Product 1

HCID 39158632HCID 39158632, compoundYield 103.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 4-phenylphenol (10.0 g, 59 mmol) in dry N,N-dimethyl-formamide (45 mL) kept under an atmosphere of nitrogen, sodium hydride (2.82 g, 71 mmol, 60% dispersion in oil) was added in portions and the reaction mixture was stirred until gas evolution ceased. A solution of m-cyanobenzyl bromide (13 g, 65 mmol) in dry N,N-dimethylformamide (45 mL) was added dropwise and the reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was poured on to ice water (150 mL). The precipitate was filtered of and washed with 50% ethanol (3×50 mL), ethanol (2×50 mL), diethyl ether (80 mL), and dried in vacuo at 50° C. for 18 hours affording crude 17.39 g of 3-(biphenyl-4-yloxymethyl)benzonitrile as a solid.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 18 hours
  2. filtrationThe precipitate was filtered of and
  3. washwashed with 50% ethanol (3×50 mL), ethanol (2×50 mL), diethyl ether (80 mL)
  4. customdried in vacuo at 50° C. for 18 hours

Sources & evidence

ORD record
ord-de360722513f4161b4d405e5282528b5
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Reaction notes

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