Triethylamine → 3-(4-Bromophenyl)-2-propenoyl azide

HRID 551271Notes

Reaction equation

HRID 551271 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8](O)=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC)=O.[N-:26]=[N+:27]=[N-:28].[Na+]>CC(C)=O.O>[Br:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([N:26]=[N+:27]=[N-:28])=[O:9])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 99777p-Bromocinnamic acid

Product 1

HCID 539034243-(4-Bromophenyl)-2-propenoyl azideYield 95.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

4-Bromocinnamic acid (7.45 g, 32.8 mmol) dissolved in acetone (150 mL) and stirred under nitrogen at 0° C. during addition of triethylamine (5.5 ml, 39.4 mmol), followed by ethyl chloroformate (3.76 ml, 39.4 mmol). Stirred reaction mixture at 0° C. for 1 hour, before adding a solution of sodium azide (3.19 g, 49.2 mmol) in water (16 mL) dropwise. Stirred reaction mixture at 0° C. for 1 hour, then room temperature for 1 hour, before pouring into water (1 L). The white precipitate was collected and washed repeatedly with water and dried (high vacuum, P2O5) to give 3-(4-bromophenyl)acryloyl azide (7.91 g, 31.3 mmol). 1H NMR (CDCl3) δ 7.66 (d, 1H), 7.55 (d, 2H), 7.40 (d, 2H), 6.41 (d, 1H). ESI MS (M+1)+: 251, 253 (Br).

Workup

  1. customreaction mixture at 0° C. for 1 hour
  2. stirringStirred
  3. customreaction mixture at 0° C. for 1 hour
  4. customThe white precipitate was collected
  5. washwashed repeatedly with water
  6. dry with materialdried (high vacuum, P2O5)

Sources & evidence

ORD record
ord-3c3b58a05bde4ef98548df9d58a77c8a
Source dataset
uspto-grants-2011_05
Patent number
US07947684B2

Reaction notes

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