Triethylamine → HCID 18963870, compound

HRID 2281872Notes

Reaction equation

HRID 2281872 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[C:10]([OH:12])=O)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.C1(P([N:34]=[N+:35]=[N-:36])(C2C=CC=CC=2)=O)C=CC=CC=1>C1(C)C=CC=CC=1>[N:34]([C:10](=[O:12])/[CH:9]=[CH:8]/[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)=[N+:35]=[N-:36]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 776461m-Bromocinnamic acid

Product 1

HCID 18963870HCID 18963870, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of (E)-3-(3-bromophenyl)acrylic acid (100 g, 0.44 mol) and triethylamine (0.48 mol) in toluene (1000 mL) was added diphenylphosphoryl azide (127.4 g, 0.45 mol) dropwise at 0-10° C. The mixture was stirred at room temperature overnight. Thin layer chromatography (petroleum ether/ethyl acetate=8:1) indicated completion of reaction. The resulting mixture was washed with 1N sodium hydroxide (500 mL) and extracted with ethyl acetate (2000 mL×3). The organic layer was concentrated to give crude (E)-1-azido-3-(3-bromophenyl)prop-2-en-1-one, which was used in the next step directly.

Workup

  1. customcompletion of reaction
  2. washThe resulting mixture was washed with 1N sodium hydroxide (500 mL)
  3. extractionextracted with ethyl acetate (2000 mL×3)
  4. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-a4d197e8287045e781d343ecad25520d
Source dataset
uspto-grants-2015_09
Patent number
US09139587B2

Reaction notes

Loading…