4-Bromobiphenyl → HCID 69203692, compound

HRID 2374125Notes

Reaction equation

HRID 2374125 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:18][CH:19]([CH2:24][CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:20][C:21](Cl)=O.C([SiH](CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:21][CH2:20][CH:19]([CH3:18])[CH2:24][CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 71014-BromobiphenylHCID 12052TriethylsilaneHCID 6451240Aluminum(III) ChlorideHCID 138457513,7-Dimethyloctanoyl Chloride

Product 1

HCID 69203692HCID 69203692, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-bromo-biphenyl (7.00 g, 0.030 mol), aluminium chloride (4.40 g, 0.033 mol) and 3,7-dimethyloctanoyl chloride (step 2) (6.90 g, 0.036 mol), in dry DCM was prepared at room temperature. The stirring reaction mixture was left to react at room temperature until g.l.c. and t.l.c. analyses revealed a complete reaction, the reaction mixture was then treated with triethylsilane (9.30 g, 0.080 mol) and left stirring overnight. The reaction product was extracted into DCM (2×100 ml) and the combined organic layers were washed with brine, water and dried (MgSO4). The product was adsorbed onto silica gel and purified by column chromatography [DCM] and recrystallised from ethanol to yield a white powder.

Workup

  1. customThe stirring reaction mixture
  2. waitwas left
  3. customto react at room temperature until g.l.c
  4. customa complete reaction
  5. waitleft
  6. extractionThe reaction product was extracted into DCM (2×100 ml)
  7. washthe combined organic layers were washed with brine, water
  8. dry with materialdried (MgSO4)
  9. custompurified by column chromatography [DCM]
  10. customrecrystallised from ethanol
  11. customto yield a white powder

Sources & evidence

ORD record
ord-1ff4879fe1b14a818d3ca2bc5e0961fe
Source dataset
uspto-grants-2008_12
Patent number
US07462427B2

Reaction notes

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