Bromomethylstyrene → HCID 15063348, compound

HRID 2110567Notes

Reaction equation

HRID 2110567 reaction equation
[CH2:1](Br)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[In].[OH:12][C:13]1[C:14](=[O:24])[C:15]2[C:20]([C:21](=[O:23])[CH:22]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2>CN(C)C=O>[OH:24][C:14]1([CH2:1]/[CH:2]=[CH:3]/[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:21]([OH:23])=[CH:22][C:13]1=[O:12]

Participants

5

Reactant 3

HCID 98116BromomethylstyreneHCID 5359967IndiumHCID 178516607HCID 178516607, compound

Product 1

HCID 15063348HCID 15063348, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Cinnamyl bromide (0.43 g, 2.2 mmol) was added to a suspension of indium metal (0.17 g, 1.5 mmol) in N,N-dimethylformamide (1 mL) at 25° C. for 0.5 h causing dissolution of the metal. 2-Hydroxy-1,4-naphthoquinone (0.25 g, 1.5 mmol) was dissolved in N,N-dimethylformamide (1 mL) and added to the mixture. After 0.5 h the mixture was partitioned between 1% HCl and ethyl acetate. The orgamic layer was separated, washed with water, brine, dried over sodium sulfate and the solvents were evaporated. The crude residue was purified using BioTage 12L column and 5% methanol/dichloromethane to give the title compound (40 mg, 10% yield).

Workup

  1. dissolutiondissolution of the metal
  2. additionadded to the mixture
  3. customAfter 0.5 h the mixture was partitioned between 1% HCl and ethyl acetate
  4. customThe orgamic layer was separated
  5. washwashed with water, brine
  6. dry with materialdried over sodium sulfate
  7. customthe solvents were evaporated
  8. customThe crude residue was purified

Sources & evidence

ORD record
ord-1997f42f27e54e98a4dd72e044c540bf
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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