Benzyl Bromide → 5-(Benzyloxy)-2-bromobenzonitrile

HRID 1474677Notes

Reaction equation

HRID 1474677 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:9]#[N:10].C([O-])([O-])=O.[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C.O>[CH2:17]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([CH:4]=1)[C:9]#[N:10])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 153231112-Bromo-5-hydroxybenzonitrile

Product 1

HCID 121019865-(Benzyloxy)-2-bromobenzonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-bromo-3-cyanophenol (1 g, 5.05 mmol) was dissolved in DMF (10 ml) and K2CO3 (1.40 g, 10.10 mmol) and benzyl bromide (0.66 ml, 5.56 mmol) added. The mixture was stirred under N2 for 1 hr at RT. The mixture was diluted with water (15 mL) and extracted with EtOAc (2×10 mL). The organic fractions were combined, washed with brine (saturated, 1×8 mL), dried over MgSO4, filtered and the volatiles removed in vacuo. The residue was purified by chromatography on silica gel Biotage 25M, using a gradient eluant of EtOAc/Hexane (0-50%) to afford the title compound. LC/MS (m/z): 289 (M+H)+.

Workup

  1. extractionextracted with EtOAc (2×10 mL)
  2. washwashed with brine (saturated, 1×8 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe volatiles removed in vacuo
  6. customThe residue was purified by chromatography on silica gel Biotage 25M

Sources & evidence

ORD record
ord-307e7b63164c4ab18b8c90b4bdcb4376
Source dataset
uspto-grants-2015_04
Patent number
US09018224B2

Reaction notes

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