tert-Butanol → HCID 66729642, compound

HRID 338991Notes

Reaction equation

HRID 338991 reaction equation
[Br:1][C:2]1[C:3]([F:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)C(O)=O.C([N:14]([CH2:17]C)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:26])=CC=1.[CH3:36][C:37]([OH:40])([CH3:39])[CH3:38]>>[Br:1][C:2]1[C:3]([F:11])=[C:4]([NH:14][C:17](=[O:26])[O:40][C:37]([CH3:39])([CH3:38])[CH3:36])[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 27363133-Bromo-2-fluorobenzoic acid

Product 1

HCID 66729642HCID 66729642, compoundYield 66%

Procedure

A solution of 3-bromo-2-fluorobenzoic acid (6.86 g, 31.32 mm 1), triethylamine (5.24 mL, 37.59 mmol) and DPPA (7.45 mL, 34.46 mmol) in t-BuOH (30 mL) was stirred at reflux for 20 hours. After cooling to ambient temperature, the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (100 mL), washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (4:1 hexane/ethyl acetate) to give tert-butyl 3-bromo-2-fluorophenylcarbamate (6.0 g, 66.0%) as an oil.

Workup

  1. temperatureat reflux for 20 hours
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate (100 mL)
  4. washwashed with brine
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography on silica gel (4:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-29ef383581644940aceb6c9b9fade95a
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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