O-Xylene → HCID 86665042, compound

HRID 1047146Notes

Reaction equation

HRID 1047146 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9](=[O:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:5]([Cl:8])=[N:6][CH:7]=1.[CH:17](OCC)(OCC)[O:18][CH2:19][CH3:20].C1(C)C(C)=CC=CC=1>C(OC(=O)C)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:9](/[C:10](=[CH:17]/[O:18][CH2:19][CH3:20])/[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:16])[C:5]([Cl:8])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 31214Ethyl orthoformateHCID 86665041HCID 86665041, compound2×

Product 1

HCID 86665042HCID 86665042, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
130 °C

Procedure

Ethyl 3-(5-bromo-2-chloropyridin-3-yl)-3-oxopropanoate (Intermediate 12, 1.0 g, 3.26 mmol) was suspended in acetic anhydride (0.83 g, 8.16 mM) and 1,1′,1″-[methanetriyltris(oxy)]triethane (0.725 g, 4.90 mmol) was added. The reaction mixture was heated to 130° C. for 3 h then cooled to room temperature and concentrated under reduced pressure. The residue so obtained was co-distilled with xylene (2-3 times) to obtain ethyl (2Z)-2-[(5-bromo-2-chloropyridin-3-yl)carbonyl]-3-ethoxyprop-2-enoate (1.1 g) which was taken without further purification to the next step.

Workup

  1. temperaturethen cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe residue so obtained

Sources & evidence

ORD record
ord-9e2984a85ac14806bfebd2896ebca2a9
Source dataset
uspto-grants-2013_10
Patent number
US08569484B2

Reaction notes

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