Triethylamine → (trans)-2-(4-Bromophenyl)cyclopropanecarbonyl azide

HRID 1470546Notes

Reaction equation

HRID 1470546 reaction equation
ClC(OCC)=O.[Br:7][C:8]1[CH:13]=[CH:12][C:11]([C@@H:14]2[CH2:16][C@H:15]2[C:17]([OH:19])=O)=[CH:10][CH:9]=1.CCN(CC)CC.[N-:27]=[N+:28]=[N-:29].[Na+]>CC(C)=O.O>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([C@@H:14]2[CH2:16][C@H:15]2[C:17]([N:27]=[N+:28]=[N-:29])=[O:19])=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 12586658rac-(1R,2R)-2-(4-bromophenyl)cyclopropane-1-carboxylic acid2×

Product 1

HCID 86691190(trans)-2-(4-Bromophenyl)cyclopropanecarbonyl azideYield 91.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Ethyl chloroformate (1.9 mL) was added to a solution of (trans)-2-(4-bromophenyl)cyclopropanecarboxylic acid (Intermediate C, 4 g, 0.0165 mol) and Et3N (2.51 mL, 0.0199 mol) in acetone (60 mL) at −20° C., stirred at same temperature for 1 h, then a solution of NaN3 (1.3 g, 0.0199 mol) in water (5 mL), was added and stirred for 30 mins at rt. After completion of reaction, checked by TLC, the solvent was evaporated and crude residue was dissolved in ethyl acetate (100 mL), washed with water (40 mL), dried over anhydrous Na2SO4, filtered and evaporated to get (trans)-2-(4-bromophenyl)cyclopropanecarbonyl azide (4 g). The crude residue is carried to next step without further purification.

Workup

  1. stirringstirred for 30 mins at rt
  2. customAfter completion of reaction
  3. customthe solvent was evaporated
  4. dissolutioncrude residue was dissolved in ethyl acetate (100 mL)
  5. washwashed with water (40 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-c44a0f9004ec48a89bf4928945d7f2fc
Source dataset
uspto-grants-2015_04
Patent number
US09006449B2

Reaction notes

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