Bromine → 3'-Bromo-4'-methoxy-1,1'-biphenyl-4-carbaldehyde

HRID 493479Notes

Reaction equation

HRID 493479 reaction equation
[Br:1]Br.[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]=[O:18])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1>CC(O)=O>[Br:1][C:10]1[CH:9]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]=[O:18])=[CH:13][CH:12]=2)[CH:7]=[CH:6][C:5]=1[O:4][CH3:3]

Participants

4

Reactant 2

HCID 24408BromineHCID 13944874'-Methoxy-(1,1'-biphenyl)-4-carboxaldehyde

Product 1

HCID 576816103'-Bromo-4'-methoxy-1,1'-biphenyl-4-carbaldehydeYield 96%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Bromine (8.2 mL, 0.160 mol) in 40 mL of glacial HOAc was added under nitrogen dropwise over 30 minutes to a solution of 4′-methoxy-1,1′-biphenyl-4-carbaldehyde (31.0g, 0.146 mol), prepared in the previous step, in 500 mL of glacial HOAc at room temperature. After the addition the reaction was stirred at room temperature for 16 h. During the reaction a solid precipitated. The solid can be collected by filtration. If by TLC starting material remains in either the solid or filtrate the solid can be redissolved and additional bromine added until the reaction is complete. When the reaction is complete by TLC, water is added and the solid present is collected by filtration to give 3′-bromo-4′-methoxy-1,1′-biphenyl-4-carbaldehyde (40.8 g, 96%) as a white solid, MS (ESI) m/z 290. Elemental Analysis for C14H11BrO2. Calc'd: C, 57.76; H, 3.81; N, 0.00. Found: C, 57.30; H, 3.61; N, 0.00.

Workup

  1. additionAfter the addition the reaction
  2. customDuring the reaction a solid
  3. customprecipitated
  4. filtrationThe solid can be collected by filtration
  5. dissolutioncan be redissolved
  6. additionadditional bromine added until the reaction
  7. additionis added
  8. filtrationthe solid present is collected by filtration

Sources & evidence

ORD record
ord-0a1978b31d8f45b89dcb1093dcb980fc
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Reaction notes

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