Methyl chloroformate → HCID 59394984, compound

HRID 471900Notes

Reaction equation

HRID 471900 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[OH:10])[CH3:2].C(N(CC)CC)C.Cl[C:19]([O:21][CH3:22])=[O:20]>CN(C1C=CN=CC=1)C.ClCCl>[C:19](=[O:20])([O:21][CH3:22])[O:10][C:4]1[CH:5]=[CH:6][C:7]([F:9])=[CH:8][C:3]=1[CH2:1][CH3:2]

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 27371852-ethyl-4-fluorophenol

Product 1

HCID 59394984HCID 59394984, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2-Ethyl-4-fluorophenol (2 g, 14.27 mmol) and DMAP (87 mg, 0.71 mmol) was dissolved in dichloromethane (10 mL) and triethylamine (4 mL, 28.5 mmol), cooled to 0° C., then treated with methyl chloroformate (2.02 g, 1.65 mL, 21.40 mmol) and allowed to warm to room temperature over 2 h. The reaction was quenched with water, the layers separated, and the aqueous layer was extracted with dichloromethane. The combined organic extracts were dried over Na2SO4, filtered and concentrated. Purification by silica gel chromatography (20% ethyl acetate/hexane) provided 2-ethyl-4-fluorophenyl methyl carbonate (2.4 g, 85% yield). 1H NMR (400.0 MHz, DMSO-d6) δ 7.26-7.17 (m, 2H), 7.12-7.07 (m, 1H), 5.76 (s, 1H), 3.83 (d, J=4.3 Hz, 2H), 2.54-2.48 (m, 2H), 1.12 (t, J=7.6 Hz, 3H).

Workup

  1. customThe reaction was quenched with water
  2. customthe layers separated
  3. extractionthe aqueous layer was extracted with dichloromethane
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4f416ba7dd534101abc16f3727b3338c
Source dataset
uspto-grants-2014_01
Patent number
US08633189B2

Reaction notes

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