Ethyl orthoformate → HCID 67517645, compound

HRID 2173393Notes

Reaction equation

HRID 2173393 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[C:4]([Br:12])[CH:3]=1.[CH:13](OCC)(OCC)OCC.[N-:23]=[N+:24]=[N-:25].[Na+]>CC(O)=O>[Br:12][C:4]1[CH:3]=[C:2]([N:1]2[CH:13]=[N:25][N:24]=[N:23]2)[CH:7]=[CH:6][C:5]=1[CH2:8][C:9]([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 12404389HCID 12404389, compound

Product 1

HCID 67517645HCID 67517645, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A solution of (4-amino-2-bromophenyl)acetic acid (230 mg, 1 mmol) and triethyl orthoformate (444 mg, 3 mmol) in 8 mL of HOAc was added sodium azide (80 mg, 1.2 mmol), and the mixture was heated to 100° C. for 3 hours. The reaction mixture was cooled to ambient temperature and the solvent was removed under vacuum. The residue was dissolved in EtOAc, washed with water, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by prep-TLC to afford [2-bromo-4-(1H-tetrazol-1-yl)phenyl]acetic acid. 1H-NMR (300 MHz, MeOD) δ ppm 9.78 (s, 1H), 8.16 (s, 1H), 7.83˜7.87 (m, 1H), 7.60˜7.63 (m, 1H), 3.89 (s, 2H).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customthe solvent was removed under vacuum
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by prep-TLC

Sources & evidence

ORD record
ord-1d45739b775d4e0fadb359af5d83fc15
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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