1-Hydroxybenzotriazole → Methyl 4-(2-bromoethyl)benzoate

HRID 11840Notes

Reaction equation

HRID 11840 reaction equation
[Br:1][CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1.[CH3:13]CN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CO>[Br:1][CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([O:10][CH3:13])=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 1040684-(2-Bromoethyl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 10586287Methyl 4-(2-bromoethyl)benzoateYield 78.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Commercially available 4-bromoethylbenzoic acid (997.9 mg) was dissolved in methanol (30 ml). After the addition of WSCI hydrochloride (1.2527 g) and HOBt (598.5 mg), the solution was stirred for 24 hours at 60° C. After the reaction, the solvent was removed by distillation. The residue was dissolved in chloroform, washed with 1 mol/l hydrochloric acid, 1 mol/l aqueous solution of sodium hydroxide, and saturated brine, and dried over anhydrous sodium sulfate. The solvent was removed by distillation and the residue was purified by silica gel column chromatography to obtain the title compound (829.5 mg) as a colorless solid.

Workup

  1. customAfter the reaction
  2. customthe solvent was removed by distillation
  3. dissolutionThe residue was dissolved in chloroform
  4. washwashed with 1 mol/l hydrochloric acid, 1 mol/l aqueous solution of sodium hydroxide, and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed by distillation
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3ccd70d7c63d4afe90a7dd07edba6d48
Source dataset
uspto-grants-2006_08
Patent number
US07098215B2

Reaction notes

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