Boron tribromide → Methyl 2-ethyl-4-hydroxy-3-methylbenzoate

HRID 388785Notes

Reaction equation

HRID 388785 reaction equation
[CH2:1]([C:3]1[C:12]([CH3:13])=[C:11]([O:14]C)[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([C:3]1[C:12]([CH3:13])=[C:11]([OH:14])[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6])[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 58298861HCID 58298861, compound

Product 1

HCID 58298869Methyl 2-ethyl-4-hydroxy-3-methylbenzoateYield 100.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.0 g of methyl 2-ethyl-4-methoxy-3-methylbenzoate are dissolved in 50 ml of DCM in a 100 ml round-bottomed flask, and BBr3 is carefully added dropwise at 0° C. The mixture is left to stir at RT for 4 hours. The solvent is distilled off in vacuo, methanol is carefully added to the residue at 0° C., and the mixture is evaporated again in a rotary evaporator. This operation is repeated a further twice, giving 1.88 g of methyl 2-ethyl-4-hydroxy-3-methylbenzoate as oil, which is employed for the next step without further purification; MS-FAB (M+H+)=195,2; Rf (polar method): 1.96 min.

Workup

  1. waitThe mixture is left
  2. distillationThe solvent is distilled off in vacuo, methanol
  3. additionis carefully added to the residue at 0° C.
  4. customthe mixture is evaporated again in a rotary evaporator

Sources & evidence

ORD record
ord-0d8ce31302db43a3bd50894d02318790
Source dataset
uspto-grants-2013_02
Patent number
US08377975B2

Reaction notes

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