Dichloromethane → HCID 86716086, compound

HRID 627520Notes

Reaction equation

HRID 627520 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.[C:10]1([CH:16]([C:20](O)=O)C(O)=O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O=P(Cl)(Cl)[Cl:25].[Al].[NH4+].[OH-].[CH2:31]([Cl:33])Cl>>[Br:1][C:2]1[CH:8]=[C:7]2[C:5](=[C:4]([F:9])[CH:3]=1)[N:6]=[C:20]([Cl:25])[C:16]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[C:31]2[Cl:33]

Participants

7

Reactant 6

HCID 6344DichloromethaneHCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 75791Phenylmalonic acidHCID 1230504-Bromo-2-fluoroanilineHCID 5359268Aluminum

Product 1

HCID 86716086HCID 86716086, compound

Procedure

A mixture of 4-bromo-2-fluoroaniline (6.53 g, 34.4 mmol), 2-phenylmalonic acid (7.43 g, 41.2 mmol), and POCl3 (31.9 mL, 344 mmol) was stirred at reflux (130° C. aluminum block temp) for 45 min. The resulting homogeneous dark solution was chilled on an ice bath, diluted with DCM (50 mL) and ice (100 mL), and stirred on the ice bath while 15 M NH4OH (30 mL) was added intermittently with swirling over ˜5 min (delayed exotherm). The aqueous layer was extracted with DCM (1×25 mL), and the combined organic layers were dried (Na2SO4), filtered, and concentrated. The residue was flash chromatographed with a 20% to 50% DCM/heptane gradient to provide the title compound as a light yellow solid.

Workup

  1. temperatureThe resulting homogeneous dark solution was chilled on an ice bath
  2. additionwas added intermittently
  3. extractionThe aqueous layer was extracted with DCM (1×25 mL)
  4. dry with materialthe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed with a 20% to 50% DCM/heptane gradient

Sources & evidence

ORD record
ord-a6d4fd113a9f4f779559bc516bf6edfd
Source dataset
uspto-grants-2016_04
Patent number
US09309222B2

Reaction notes

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