Methyl chloroformate → Methyl 2-(trifluoromethoxy)phenyl carbonate

HRID 471924

Reaction equation

HRID 471924 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10].C(N(CC)CC)C.Cl[C:21]([O:23][CH3:24])=[O:22]>C(Cl)Cl>[C:21](=[O:22])([O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[O:3][C:2]([F:11])([F:12])[F:1])[O:23][CH3:24]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 27772992-(Trifluoromethoxy)phenol

Product 1

HCID 59395054Methyl 2-(trifluoromethoxy)phenyl carbonateYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-(Trifluoromethoxy)phenol (6.0 g, 32.7 mmol) was dissolved in methylene chloride and triethylamine (9.1 mL, 65.4 mmol). The mixture was cooled to 0° C. and methyl chloroformate (2.8 mL, 36.0 mmol) was added dropwise. The mixture was stirred for 2 h at room temperature then quenched with saturated NH4Cl. The reaction was diluted with water and the aqueous layer extracted with dichloromethane (2×30 mL). The combined extracts were washed with water (100 mL) and brine (100 mL), dried over MgSO4, filtered and concentrated in vacuo to provide methyl 2-(trifluoromethoxy)phenyl carbonate (7.1 g, 92% yield). 1H NMR (400.0 MHz, DMSO-d6) δ7.36-7.26 (m, 4H), 3.93 (s, 3H).

Workup

  1. customthen quenched with saturated NH4Cl
  2. additionThe reaction was diluted with water
  3. extractionthe aqueous layer extracted with dichloromethane (2×30 mL)
  4. washThe combined extracts were washed with water (100 mL) and brine (100 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-700cfeb0cd194b2699109474c673a4f7
Source dataset
uspto-grants-2014_01
Patent number
US08633189B2

Linked notes

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