Cyclopropanecarbonyl chloride → 2-Amino-5-bromo-3-cyano-6-fluoro-4-methylphenyl acetate

HRID 17328

Reaction equation

HRID 17328 reaction equation
[NH2:1][C:2]1[C:9]([OH:10])=[C:8]([F:11])[C:7]([Br:12])=[C:6]([CH3:13])[C:3]=1[C:4]#[N:5].C(N(C(C)C)CC)(C)C.[CH:23]1([C:26](Cl)=[O:27])CC1>C(OCC)(=O)C>[C:26]([O:10][C:9]1[C:8]([F:11])=[C:7]([Br:12])[C:6]([CH3:13])=[C:3]([C:4]#[N:5])[C:2]=1[NH2:1])(=[O:27])[CH3:23]

Participants

5

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 860975142-Amino-5-bromo-4-fluoro-3-hydroxy-6-methylbenzonitrile

Product 1

HCID 860975162-Amino-5-bromo-3-cyano-6-fluoro-4-methylphenyl acetateYield 97.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

2-Amino-5-bromo-4-fluoro-3-hydroxy-6-methylbenzonitrile (I-75) (7.86 g, 32.08 mmol) and diisopropylethylamine (19.5 ml, 112.2 mmol) were dissolved in ethyl acetate (300 ml), and at 0° C., cyclopropanecarbonyl chloride (4.4 ml, 48.12 mmol) was dropwise added, followed by stirring at room temperature for 16 hours under nitrogen atmosphere. After the reaction, ethyl acetate was added to the reaction liquid, followed by washing with water and saturated brine. The organic layer was concentrated under reduced pressure, the resulting residue was recrystallized with diisopropyl ether/ethyl acetate to obtain the entitled compound (8.96 g, 89%) as a white solid.

Workup

  1. additionwas added to the reaction liquid
  2. washby washing with water and saturated brine
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customthe resulting residue was recrystallized with diisopropyl ether/ethyl acetate

Sources & evidence

ORD record
ord-26668f8c13a84f17b4fc2b4a1d1a64da
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Linked notes

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