Hydrochloric Acid → HCID 69726416, compound

HRID 2306553Notes

Reaction equation

HRID 2306553 reaction equation
[CH3:1][C:2]1[C:11](Br)=[C:10]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][C:14]=2Br)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[Li+].[Cl-:25].[ClH:26]>CN(C=O)C>[CH3:1][C:2]1[C:11]([Cl:25])=[C:10]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][C:14]=2[Cl:26])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 433294Lithium ChlorideHCID 53784417HCID 53784417, compound

Product 1

HCID 69726416HCID 69726416, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(R)-2,2′-Dibromomethyl-1,1′-binaphthyl (4, 40 g, 90.8 mmol) and LiCl (30 g, 707 mmol) in DMF (800 mL) was mixed together and stirred at room temperature for 6 h. To this mixture was added carefully 5% aqueous HCl (300mL) (exothermomic reaction occurred). The mixture was then extracted with ether (4×400 mL). The organic layer was dried over sodium sulfate, concentrated and recrystallized from CH2Cl2/hexane to gave 5 as white solid (30 g, 93%).

Workup

  1. extractionThe mixture was then extracted with ether (4×400 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated
  4. customrecrystallized from CH2Cl2/hexane

Sources & evidence

ORD record
ord-f851f1ce20df4733a407c3de6d32dd24
Source dataset
uspto-grants-2004_12
Patent number
US06828271B2

Reaction notes

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