Benzene → 2,4-Dichlorobenzoyl chloride

HRID 2177650

Reaction equation

HRID 2177650 reaction equation
CC(NC(=O)[C:7]1[CH:12]=[CH:11][CH:10]=[C:9](C(F)(F)F)[C:8]=1[Cl:17])C#C.N1[N:23]2[CH:24]=[CH:25][CH:26]=[N:27][C:22]2=[N:21]N=1.[Cl:28][C:29]1[CH:37]=[C:36](F)[CH:35]=[CH:34][C:30]=1[C:31]([Cl:33])=[O:32].[CH3:39][CH2:40]N(C(C)C)C(C)C.[CH:48]1C=CC=C[CH:49]=1.C(Br)C=C>>[Cl:28][C:29]1[CH:37]=[C:36]([Cl:17])[CH:35]=[CH:34][C:30]=1[C:31]([Cl:33])=[O:32].[CH2:48]([C:22]1[N:27]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:26]2[CH:25]=[CH:24][N:23]=[CH:40][C:39]=2[N:21]=1)[CH3:49]

Participants

8

Reactant 6

HCID 241BenzeneHCID 7841Allyl bromideHCID 81531DiisopropylethylamineHCID 349391Tetrazolo[1,5-a]pyrimidineHCID 27365462-Chloro-4-fluorobenzoyl chlorideHCID 90409423N-(1-Methylpropargyl)-2-chloro-3-(trifluoromethyl)benzamide

Product 2

HCID 666452,4-Dichlorobenzoyl chlorideYield 52%HCID 904095952-ethyl-1-phenyl-1H-imidazo[4,5-c]pyridineYield 25%

Procedure

To the suspension of compound Intermediate 233 (138 mg, 0.5 mmol, 1.0 equiv), tetrazolo[1,5-a]pyrimidine (Intermediate 234) (67 mg, 0.55 mmol, 1.1 equiv.) and Hunig's base (0.3 mL, 1.75 mmol, 3.5 equiv.), (CuOTf)2.Benzene (150 mg, 0.6 mmol, 1.2 equiv.) was added at room temperature in one portion under N2. After 6 hours at room temperature, HPLC analysis indicated the complete consumption of Intermediate 233. Allyl bromide (242 mg, 2.0 mmol, 4.0 equiv.) was added and the reaction solution was stirred for another 2 hours. The same workup/purification procedure were followed to afford Intermediate 235 (113 mg, 0.26 mml, 52% yield) along with Intermediate 236 (49 mg, 0.12 mmol, 25% yield).

Workup

  1. customthe complete consumption of Intermediate 233
  2. customThe same workup/purification procedure

Sources & evidence

ORD record
ord-03aa78ecac6f469996ac905835467438
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Linked notes

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