Methyl chloroformate → Methyl (4-bromo-2-fluorobenzyl)carbamate

HRID 1257841Notes

Reaction equation

HRID 1257841 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[Br:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][NH2:14])=[C:9]([F:15])[CH:8]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:5][O:4][C:2](=[O:3])[NH:14][CH2:13][C:10]1[CH:11]=[CH:12][C:7]([Br:6])=[CH:8][C:9]=1[F:15]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 3770848(4-Bromo-2-fluorophenyl)methanamine

Product 1

HCID 19695032Methyl (4-bromo-2-fluorobenzyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl chloroformate (85.0 μL, 1.1 mmol) was added to a solution of 1-(4-bromo-2-fluorophenyl)methanamine (0.204 g, 1.0 mmol) and triethylamine (148.1 μL, 1.1 mmol) in methylene chloride (5 mL) at 0° C. After 10 min, the ice-water bath was removed. The mixture was stirred at RT for 1 h, washed with water, and brine. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue (220 mg, 83.9%) was directly used in next step without further purification. LCMS: (M+H)=263.9/261.8.

Workup

  1. customthe ice-water bath was removed
  2. washwashed with water, and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue (220 mg, 83.9%) was directly used in next step without further purification

Sources & evidence

ORD record
ord-018cfa94993f48388c9742b39d74a472
Source dataset
uspto-grants-2013_06
Patent number
US08461330B2

Reaction notes

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