Diethyl Ether → Methyl 4-(2-bromoethyl)benzoate

HRID 1532977Notes

Reaction equation

HRID 1532977 reaction equation
[Br:1][CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1.[CH3:13]COCC.[N+](=C)=[N-]>C1COCC1>[Br:1][CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([O:10][CH3:13])=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 9550DiazomethaneHCID 1040684-(2-Bromoethyl)benzoic acid

Product 1

HCID 10586287Methyl 4-(2-bromoethyl)benzoateYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 9.16 g (40 mmol) of 4-(2-bromoethyl)benzoic acid in 100 mL of THF was combined with an ether solution containing excess diazomethane. The excess diazomethane was consumed by addition of glacial acetic acid and the resultant solution was concentrated, in vacuo. The residue obtained was partitioned between saturated NaHCO3 (150 mL) and ethyl acetate (150 ml). The layers were separated and the aqueous phase was extracted with ethyl acetate (70 mL). The combined organic extracts were dried over Na2SO4 and concentrated in vacuo, yielding the product as a yellow oil (9.65 g, 99% yield).

Workup

  1. customThe excess diazomethane was consumed by addition of glacial acetic acid
  2. concentrationthe resultant solution was concentrated, in vacuo
  3. customThe residue obtained
  4. customwas partitioned between saturated NaHCO3 (150 mL) and ethyl acetate (150 ml)
  5. customThe layers were separated
  6. extractionthe aqueous phase was extracted with ethyl acetate (70 mL)
  7. dry with materialThe combined organic extracts were dried over Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-017a2ff18c134c23bb5f3229a408d042
Source dataset
uspto-grants-2001_03
Patent number
US06207670B1

Reaction notes

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