tert-Butanol → HCID 58072166, compound

HRID 1895203Notes

Reaction equation

HRID 1895203 reaction equation
[F:1][CH:2]([F:14])[O:3][C:4]1[CH:12]=[CH:11][C:7](C(O)=O)=[C:6]([F:13])[CH:5]=1.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:22])=CC=1.CC[N:34]([CH2:37]C)CC.[CH3:39][C:40]([OH:43])([CH3:42])[CH3:41]>>[F:14][CH:2]([F:1])[O:3][C:4]1[CH:12]=[CH:11][C:7]([NH:34][C:37](=[O:22])[O:43][C:40]([CH3:42])([CH3:41])[CH3:39])=[C:6]([F:13])[CH:5]=1

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 201120794-(Difluoromethoxy)-2-fluorobenzoic acid

Product 1

HCID 58072166HCID 58072166, compoundYield 63%

Procedure

A solution of 4-(difluoromethoxy)-2-fluorobenzoic acid (1 g, 4.85 mmol), DPPA (1.6 g, 5.83 mmol) and Et3N (0.59 g, 5.83 mmol) in 16 mL of t-BuOH was refluxed for 4 h, and then concentrated. The residue was dissolved in dichloromethane (40 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 (850 mg, yield 63%) as a yellow solid: 1H NMR (400 MHz, CDCl3): δ ppm 1.53 (s, 9H), 6.44 (t, J=73.6 Hz, 1H), 6.89-6.92 (m, 1H), 7.24-7.27 (m, 1H), 7.37-7.41 (m, 1H).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in dichloromethane (40 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-abd02294cf394055a09cf41f12708e7e
Source dataset
uspto-grants-2013_08
Patent number
US08513251B2

Reaction notes

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