Hydrochloric Acid → HCID 12620059, compound

HRID 1351071Notes

Reaction equation

HRID 1351071 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[H-].[Na+].[Br:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15]Br.Cl>C1COCC1.O>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][O:5][CH2:15][C:14]1[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=1[Br:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 728502-Bromobenzyl alcoholHCID 769652-Bromobenzyl bromide

Product 1

HCID 12620059HCID 12620059, compoundYield 79.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

Solution of 2-bromobenzylalcohol (3.8 g) in THF (10 ml) was delivered by drops over 15 minutes to suspension of sodium hydride (0.88 g; 60% in oil) in THF (30 ml) cooled to −0° C. in argon atmosphere, and the reaction mixture was further stirred for 20 minutes. Solution of 2-bromobenzyl bromide (6.0 g) in THF (10 ml) was added thereto and the reaction solution was stirred for one hour at room temperature. The reaction mixture was poured to water and neutralized with 1N hydrochloric acid and extracted with hexane. The organic layer was dried with anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography (hexane:ethyl acetate=1:0 to 100:1 to 10:1) to obtain the title compound (5.77 g) having the following physical data.

Workup

  1. stirringthe reaction solution was stirred for one hour at room temperature
  2. extractionextracted with hexane
  3. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (hexane:ethyl acetate=1:0 to 100:1 to 10:1)

Sources & evidence

ORD record
ord-96cb6c8854b9471bb47c33a22db7d9c5
Source dataset
uspto-grants-2007_05
Patent number
US07217701B2

Reaction notes

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