Sodium Azide → HCID 86666126, compound

HRID 511681Notes

Reaction equation

HRID 511681 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH3:12])[CH2:9][O:10][CH3:11])=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].[N-:17]=[N+:18]=[N-:19].[Na+]>CN(C=O)C>[N:17]([C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH3:12])[CH2:9][O:10][CH3:11])=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15])=[N+:18]=[N-:19]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 67775403HCID 67775403, compound

Product 1

HCID 86666126HCID 86666126, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Fluoro-4-(1-methoxy-2-methylpropan-2-yl)-2-nitrobenzene (2.227 g, 9.80 mmol) was dissolved in DMF (25 ml) and sodium azide (1.274 g, 19.6 mmol) was added at r.t. and the reaction stirred overnight. The reaction was quenched with water (75 ml) and the mixture was extracted with TBME (3×75 ml). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to give the crude product. The product was purified by silica flash column chromatography using between 100% heptane to 15% EtOAc:85% heptane as eluent to give the product as a yellow oil (2.301 g, 75%, 80% pure): LC purity 79% (ret. time, 2.15 min); 1H NMR (500 MHz, CDCl3) δH 7.97 (d, J=2.2 Hz, 1H), 7.66 (dd, J=8.5, 2.2 Hz, 1H), 7.33-7.22 (m, 1H), 3.40 (s, 2H), 3.33 (s, 3H), 1.36 (s, 6H).

Workup

  1. customThe reaction was quenched with water (75 ml)
  2. extractionthe mixture was extracted with TBME (3×75 ml)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give the crude product
  7. customThe product was purified by silica flash column chromatography

Sources & evidence

ORD record
ord-ade649125da14a10a21eb9d64c08a572
Source dataset
uspto-grants-2015_08
Patent number
US09096634B2

Reaction notes

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