Diisopropylethylamine → HCID 57470997, compound

HRID 1784884Notes

Reaction equation

HRID 1784884 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([I:11])[CH:10]=1)[C:5](O)=[O:6].C(N(C(C)C)CC)(C)C.C1(P([N:35]=[N+:36]=[N-:37])(C2C=CC=CC=2)=O)C=CC=CC=1>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([I:11])[CH:10]=1)[C:5]([N:35]=[N+:36]=[N-:37])=[O:6]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 51825203-Bromo-5-iodobenzoic acid

Product 1

HCID 57470997HCID 57470997, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 3-bromo-5-iodo benzoic acid (5.0 g, 15 mmol) in methanol (30 mL) was added diisopropylethylamine (2.9 mL, 16.8 mmol) and diphenylphosphoryl azide (3.6 mL, 16.8 mmol). The reaction mixture was stirred for 12 hours at room temperature and then quenched with the addition of 100 mL water. A solid precipitated out. The solid was filtered, washed with water and dried to give 5.0 g (96%) of 3-bromo-5-iodo-benzoyl azide.

Workup

  1. customquenched with the addition of 100 mL water
  2. customA solid precipitated out
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-0bfeeb5b506a4595a50252d3877a08b5
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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