tert-Butanol → HCID 58072473, compound

HRID 1895205Notes

Reaction equation

HRID 1895205 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([O:11][C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7][C:3]=1C(O)=O.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:23])=CC=1.CC[N:35]([CH2:38]C)CC.[CH3:40][C:41]([OH:44])([CH3:43])[CH3:42]>>[F:1][C:2]1[CH:10]=[C:9]([O:11][C:12]([F:13])([F:14])[F:15])[CH:8]=[CH:7][C:3]=1[NH:35][C:38](=[O:23])[O:44][C:41]([CH3:43])([CH3:42])[CH3:40]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 580723032-Fluoro-4-(trifluoromethoxy)benzoic acid

Product 1

HCID 58072473HCID 58072473, compoundYield 50%

Procedure

A solution of 2-fluoro-4-(trifluoromethoxy)benzoic acid (3 g, 13.4 mmol), DPPA (4.4 g, 16.1 mmol) and Et3N (1.63 g, 16.1 mmol) in 130 mL of t-BuOH was refluxed for 4 h, and then concentrated. The residue was dissolved in dichloromethane (200 mL), washed with 1M HCl aqueous solution, dried over Na2SO4, and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel (petroether/AcOEt=4/1) to get the title compound (2 g, 50% yield) as a yellow solid: 1H NMR (400 MHz, CDCl3): δ ppm 1.27 (s, 9H), 6.97-7.03 (m, 1H), 7.21-7.27 (m, 1H), 7.37-7.41 (m, 1H).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in dichloromethane (200 mL)
  3. washwashed with 1M HCl aqueous solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by flash column chromatography on silica gel (petroether/AcOEt=4/1)

Sources & evidence

ORD record
ord-fedfcff7eb7b4fc583a540c4abb171f1
Source dataset
uspto-grants-2013_08
Patent number
US08513251B2

Reaction notes

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