2,3-Dichlorobenzoyl chloride → HCID 69527429, compound

HRID 890242Notes

Reaction equation

HRID 890242 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([CH3:11])=[CH:7]2.C[Mg]Br.[Cl:15][C:16]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:17]=1[C:18](Cl)=[O:19].[NH4+].[Cl-]>C1COCC1.CCOCC>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([CH3:11])=[C:7]2[C:18]([C:17]1[CH:21]=[CH:22][CH:23]=[C:24]([Cl:25])[C:16]=1[Cl:15])=[O:19]

Participants

7

Reactant 4

HCID 179442,3-Dichlorobenzoyl chlorideHCID 25517Ammonium ChlorideHCID 44130817-Bromo-2-methylindoleHCID 178418573HCID 178418573, compound

Product 1

HCID 69527429HCID 69527429, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

10.7 g of 7-bromo-2-methyl-1H-indole are placed in 100 ml of THF and the mixture is cooled to −10° C. 22 ml of 3M methylmagnesium bromide in ether are added at this temperature. The mixture is allowed to return to AT and is then cooled to −5° C. and 13.5 g of 2,3-dichlorobenzoyl chloride, dissolved in 80 ml of THF, are added dropwise. The medium is allowed to return to AT and is then poured onto a saturated NH4Cl solution. Extraction is carried out with ether and then the organic phase is washed with a 10% NaOH solution, water and a saturated NaCl solution. It is dried and evaporated and the residue is chromatographed on silica while eluting with an AcOEt/cyclohexane (10/90, v/v) mixture. The product obtained crystallizes from ether and 5 g of the expected compound are obtained.

Workup

  1. temperatureis then cooled to −5° C.
  2. additionare added dropwise
  3. extractionExtraction
  4. washthe organic phase is washed with a 10% NaOH solution, water
  5. customIt is dried
  6. customevaporated
  7. customthe residue is chromatographed on silica
  8. washwhile eluting with an AcOEt/cyclohexane (10/90
  9. customThe product obtained
  10. customcrystallizes from ether and 5 g of the expected compound
  11. customare obtained

Sources & evidence

ORD record
ord-5ce1e6b06a7f4830b3fa846e36948413
Source dataset
uspto-grants-2006_02
Patent number
US06995184B2

Reaction notes

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