Hydrochloric Acid → HCID 68491438, compound

HRID 444720Notes

Reaction equation

HRID 444720 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[F:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[F:21])[CH:16]=O.CC(OC(C)=O)=O.C(N(C(C)C)CC)(C)C.Cl>C(Cl)Cl.CO>[F:12][C:13]1[CH:14]=[C:15]([CH:16]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[C:9]([OH:11])=[O:10])[CH:18]=[CH:19][C:20]=1[F:21]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 98372-(4-Fluorophenyl)acetic acidHCID 81531DiisopropylethylamineHCID 5880883,4-Difluorobenzaldehyde

Product 1

HCID 68491438HCID 68491438, compoundYield 121.6%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of 4-fluorophenylacetic acid (2 g, 13 mmol), 3,4-difluorobenzaldehyde (2.5 g, 13 mmol), Ac2O (10 mL) and diisopropylethylamine (2.9 mL) was stirred at room temperature for 12 hours. Upon completion, as monitored by TLC using DCM:MeOH (9:1) as the eluent, 10 mL 10% aqueous HCl was added to the reaction mixture, the precipitate formed was filtered and dissolved in CH2Cl2 (100 mL). The organic layer was washed with 10% aqueous NaOH (3×50 mL) and the basic aqueous solution was acidified with 10% aqueous HCl to pH 3. The precipitate formed was filtered, washed with water (100 mL) and dried to get the product (4.4 g, 41.5% yield).

Workup

  1. additionwas added to the reaction mixture
  2. customthe precipitate formed
  3. filtrationwas filtered
  4. dissolutiondissolved in CH2Cl2 (100 mL)
  5. washThe organic layer was washed with 10% aqueous NaOH (3×50 mL)
  6. customThe precipitate formed
  7. filtrationwas filtered
  8. washwashed with water (100 mL)
  9. customdried

Sources & evidence

ORD record
ord-9fe79fb689554416a427cb2a6acc2681
Source dataset
uspto-grants-2013_07
Patent number
US08476255B2

Reaction notes

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