Methyl chloroformate → 2-Tert-butyl-4-fluorophenyl methyl carbonate

HRID 73976Notes

Reaction equation

HRID 73976 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:6]=1[OH:12])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.Cl[C:21]([O:23][CH3:24])=[O:22]>O1CCOCC1>[C:21](=[O:22])([O:23][CH3:24])[O:12][C:6]1[CH:7]=[CH:8][C:9]([F:11])=[CH:10][C:5]=1[C:1]([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 105351102-Tert-butyl-4-fluorophenol

Product 1

HCID 574702152-Tert-butyl-4-fluorophenyl methyl carbonateYield 59%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-tert-butyl-4-fluorophenol (2.63 g, 15.7 mmol) and NEt3 (3.13 mL, 22.5 mmol) in dioxane (45 mL) was added methyl chloroformate (1.27 mL, 16.5 mmol). The mixture was stirred at room temperature for 1 h. The precipitate was removed via filtration. The filtrate was then diluted with water and extracted with ether. The ether extract was washed with water and dried over MgSO4. After removal of solvent, the residue was purified by column chromatography to give 2-tert-butyl-4-fluorophenyl methyl carbonate (2.08 g, 59%). 1H NMR (400 MHz, DMSO-d6) δ 7.24 (dd, J=8.8, 5.4 Hz, 1H), 7.17-7.10 (m, 2H), 3.86 (s, 3H), 1.29 (s, 9H).

Workup

  1. customThe precipitate was removed via filtration
  2. additionThe filtrate was then diluted with water
  3. extractionextracted with ether
  4. extractionThe ether extract
  5. washwas washed with water
  6. dry with materialdried over MgSO4
  7. customAfter removal of solvent
  8. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-8e859cf41b0b4bde9cd2285517254e47
Source dataset
uspto-grants-2014_09
Patent number
US08829204B2

Reaction notes

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