Carbon tetrabromide → 4-(2,2-Dibromoethenyl)-1,1'-biphenyl

HRID 2234149Notes

Reaction equation

HRID 2234149 reaction equation
[Br:1][C:2]([Br:5])(Br)Br.[C:6]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]=[CH:10][C:9]([CH:12]=O)=[CH:8][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[Br:1][C:2]([Br:5])=[CH:12][C:9]1[CH:10]=[CH:11][C:6]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 76689(1,1'-Biphenyl)-4-carboxaldehydeHCID 516892Sodium Bicarbonate

Product 1

HCID 166411304-(2,2-Dibromoethenyl)-1,1'-biphenyl

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tetrabromomethane (21.8 g, 166 mmol) was added to a cooled solution of biphenyl-4-carbaldehyde (10.0 g, 54.9 mmol) and triphenylphosphine (35.5 g, 131.8 mmol) in dry methylene chloride (100 mL). Reaction mixture was stirred for 3 h at ambient temperature and saturated solution of sodium hydrogen carbonate (50 mL) was added. The organic layer was washed with water (50 mL), dried with anhydrous magnesium sulfate and subsequently evaporated in vacuo. The crude product was twice re-crystallized from methanol giving 1,1-dibromo-2-(4-biphenylyl)ethene as a white solid.

Workup

  1. customReaction mixture
  2. washThe organic layer was washed with water (50 mL)
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customsubsequently evaporated in vacuo
  5. customThe crude product was twice re-crystallized from methanol

Sources & evidence

ORD record
ord-0a5324338173405186a47efd28131b75
Source dataset
uspto-grants-2010_05
Patent number
US07709528B2

Reaction notes

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