Methyl chloroformate → HCID 59395084, compound

HRID 1465087Notes

Reaction equation

HRID 1465087 reaction equation
[CH:1]1([C:6]2[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:7]=2[OH:13])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:22]([O:24][CH3:25])=[O:23]>ClCCl>[C:22](=[O:23])([O:24][CH3:25])[O:13][C:7]1[CH:8]=[CH:9][C:10]([F:12])=[CH:11][C:6]=1[CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 59394940HCID 59394940, compound

Product 1

HCID 59395084HCID 59395084, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Cyclopentyl-4-fluorophenol (1.70 g, 9.43 mmol) was dissolved in dichloromethane (20 mL) and triethylamine (2.6 mL, 18.85 mmol), cooled to 0° C., then treated with methyl chloroformate (1.09 mL, 14.14 mmol) and allowed to warm to room temperature over 16 h. The reaction was quenched with 3 mL saturated NaHCO3, washed with 50% saturated NaHCO3 (1×50 mL) and brine (1×50 mL), then dried over Na2SO4. Filtration followed by concentration yielded 2-cyclopentyl-4-fluorophenyl methyl carbonate as an oil which was used for the next step without purification. 1H NMR (400.0 MHz, CDCl3) δ 7.09-7.01 (m, 2H), 6.92-6.87 (m, 1H), 3.92 (s, 3H), 3.13 (dd, J=8.4, 17.2 Hz, 1H), 2.08-2.01 (m, 2H), 1.86-1.66 (m, 4H), 1.59-1.50 (m, 2H). MS (ESI) m/z (M+H+): 239.5.

Workup

  1. customThe reaction was quenched with 3 mL saturated NaHCO3
  2. washwashed with 50% saturated NaHCO3 (1×50 mL) and brine (1×50 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationFiltration
  5. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-70efd1b58b9f466693494581c94ce257
Source dataset
uspto-grants-2015_04
Patent number
US08999976B2

Reaction notes

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