4'-Bromo-5-chlorobiphenyl-2-carbaldehyde → 4'-Bromo-5-chloro-2-vinylbiphenyl

HRID 1043425Notes

Reaction equation

HRID 1043425 reaction equation
[Li][CH2:2]CCC.[Br:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:14]([CH:20]=O)=[CH:15][CH:16]=[C:17]([Cl:19])[CH:18]=2)=[CH:9][CH:8]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[Br:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=2[CH:20]=[CH2:2])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 592665424'-Bromo-5-chlorobiphenyl-2-carbaldehydeHCID 178418339Butyllithium

Product 1

HCID 592665224'-Bromo-5-chloro-2-vinylbiphenylYield 83%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

BuLi (2.5M in hexanes, 11.3 mL, 28.2 mmol) was added to a solution of methyltriphenylphosphonium bromide (10.1 g, 28.2 mmol) in THF (65 mL). The mixture was stirred at 0° C. for 1 hr. A solution of 4′-bromo-5-chlorobiphenyl-2-carbaldehyde (4.2 g, 14.11 mmol) in THF (65 mL) was added dropwise at 0° C. The mixture was stirred overnight from 0° C. to r.t. The reaction was filtered and evaporated. The residue was diluted with diethyl ether and washed with water and brine. The ether layer was collected, dried (MgSO4), filtered and evaporated to give the crude material. The crude material was purified on the Biotage (5-15% EtOAc:Hex) to give 4′-bromo-5-chloro-2-vinylbiphenyl (3.43 g, 11.68 mmol, 83% yield) as a clear oil.

Workup

  1. stirringThe mixture was stirred overnight from 0° C. to r.t
  2. filtrationThe reaction was filtered
  3. customevaporated
  4. additionThe residue was diluted with diethyl ether
  5. washwashed with water and brine
  6. customThe ether layer was collected
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customto give the crude material
  11. customThe crude material was purified on the Biotage (5-15% EtOAc:Hex)

Sources & evidence

ORD record
ord-7d1c35633e104719b67a550b1e578ede
Source dataset
uspto-grants-2013_10
Patent number
US08563505B2

Reaction notes

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