Benzyl Bromide → HCID 15010143, compound

HRID 1033568Notes

Reaction equation

HRID 1033568 reaction equation
[Br:1][C:2]1[C:3]([C:18]#[N:19])=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[NH:5][C:6]=1[Br:7].C1COCC1.CC([O-])(C)C.[K+].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>O.CCOC(C)=O.CCCCCC>[CH2:31]([N:5]1[C:6]([Br:7])=[C:2]([Br:1])[C:3]([C:18]#[N:19])=[C:4]1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:15])([F:17])[F:16])=[CH:10][CH:9]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 8028TetrahydrofuranHCID 15010122HCID 15010122, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 15010143HCID 15010143, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

In a 100 mL flask, 1.5 g of 4,5-dibromo-2-(α,α,α-trifluoro-p-tolyl)pyrrole-3-carbonitrile is mixed with 50 mL dry THF to give a clear dark solution. 1 eq of KOtBu is added with stirring. After a few minutes the solution clears. Benzyl bromide (0.65 g) is added by syringe. The mixture is heated at reflux overnight. The following day TLC (50/50 EtOAc/hexane) indicates the presence of both starting material and product. The reaction is worked up in the following manner; 50 mL of water is added and the mixture is extracted with 4×50 mL CHCl3. The organic phases are combined and washed with 4×50 mL 10% aq. NAOH. The organic phase is dried with MgSO4 and stripped. This gives a brown solid which is crystallized from EtOAc/hexane, mp 145°-147° C.

Workup

  1. customto give a clear dark solution
  2. waitAfter a few minutes the solution clears
  3. temperatureThe mixture is heated
  4. temperatureat reflux overnight
  5. extractionthe mixture is extracted with 4×50 mL CHCl3
  6. washwashed with 4×50 mL 10% aq. NAOH
  7. dry with materialThe organic phase is dried with MgSO4
  8. customThis gives a brown solid which
  9. customis crystallized from EtOAc/hexane, mp 145°-147° C.

Sources & evidence

ORD record
ord-565e4507b00d4f2cb418c98089328b80
Source dataset
uspto-grants-1994_05
Patent number
US05310938

Reaction notes

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