Bromine → Ethyl 3′-bromo-4′-methoxy[1,1′-biphenyl]-4-carboxylate

HRID 2288697Notes

Reaction equation

HRID 2288697 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]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:10]1[CH:9]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][CH:12]=2)[CH:7]=[CH:6][C:5]=1[O:4][CH3:3]

Participants

4

Reactant 2

HCID 24408BromineHCID 2764348Ethyl 4'-methoxy[1,1'-biphenyl]-4-carboxylate

Product 1

HCID 85749597Ethyl 3′-bromo-4′-methoxy[1,1′-biphenyl]-4-carboxylate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of bromine (14.6 g, 91.3 mmol) in carbon tetrachloride (100 mL) is added to a stirred mixture of 4'-Methoxy-[1,1'-biphenyl]-4-carboxylic acid, ethyl ester (23.4 g, 91.3 mmol) and silica gal (100 g of particle size 0.040-0.063 mm; Merck 1.09385) in carbon tetrachloride (350 mL). The mixture is stirred at 20° C. for 4 h after which the silica gel is removed by filtration. The filtrate is washed with aqueous sodium hydrogen carbonate (200 mL of 1 M) followed by aqueous sodium thiosulphate (50 mL of 2 M), dried (Na2SO4), filtered and evaporated to dryness under reduced pressure to give the crude product which is recrystallised from ether-cyclohexane to give 3'-bromo-4'-methoxy-[1,1'-biphenyl]-4-carboxylic acid, ethyl ester as a colourless crystalline solid, m.p. 114-115° C.

Workup

  1. customis removed by filtration
  2. washThe filtrate is washed with aqueous sodium hydrogen carbonate (200 mL of 1 M)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated to dryness under reduced pressure
  6. customto give the crude product which
  7. customis recrystallised from ether-cyclohexane

Sources & evidence

ORD record
ord-ac908827d5b64314a20d22828dfe47fa
Source dataset
uspto-grants-2000_07
Patent number
US06090817

Reaction notes

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