Benzyl Bromide → HCID 66744472, compound

HRID 505110Notes

Reaction equation

HRID 505110 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(Cl)Cl.CO.[BH4-].[Na+]>C1(C)C=CC=CC=1.CO>[CH2:17]([N:14]1[CH2:15][CH:16]=[C:11]([C:4]2[C:5]3[O:9][CH2:8][CH2:7][C:6]=3[CH:10]=[C:2]([Br:1])[CH:3]=2)[CH2:12][CH2:13]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 4311764Sodium borohydrideHCID 21226129Dichloromethane methanolHCID 66743454HCID 66743454, compound

Product 1

HCID 66744472HCID 66744472, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-(5-bromo-2,3-dihydro-benzofuran-7-yl)-pyridine in toluene was added benzyl bromide (1 eq.) and the reaction mixture was stirred under reflux for 14 h. Reaction was monitored by TLC (CH2Cl2/MeOH 95:5) and revealed total conversion to an intermediate. Complete evaporation of the solvent gave a white solid. The solid was dissolved in MeOH under argon and cooled down to 0° C., NaBH4 (2.05 eq.) was added portion-wise (exothermic reaction) and the reaction mixture was stirred for 3 h at RT. Evaporation of MeOH, redissolution in CH2Cl2 and sequential washing with 1N NaHCO3 and brine, followed by purification by SiO2 gel chromatography (CH2Cl2/MeOH: 98/2) gave 71% yield of the tide compound.

Workup

  1. temperatureunder reflux for 14 h
  2. customReaction
  3. customComplete evaporation of the solvent
  4. customgave a white solid
  5. customportion-wise (exothermic reaction)
  6. stirringthe reaction mixture was stirred for 3 h at RT
  7. customEvaporation of MeOH, redissolution in CH2Cl2
  8. washsequential washing with 1N NaHCO3 and brine
  9. customfollowed by purification by SiO2 gel chromatography (CH2Cl2/MeOH: 98/2)

Sources & evidence

ORD record
ord-9c7da50a10044b098d39f0fc90eeaa7b
Source dataset
uspto-grants-2010_08
Patent number
US07781436B2

Reaction notes

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