Boron tribromide → Ethyl 3-hydroxy-4-methylphenylacetate

HRID 1272186Notes

Reaction equation

HRID 1272186 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:7][C:8]=1[CH3:9].B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:7][C:8]=1[CH3:9]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 21079756Ethyl 3-methoxy-4-methylphenylacetate

Product 1

HCID 21079755Ethyl 3-hydroxy-4-methylphenylacetateYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 4c (2.2 g; 8.0 mmol) and 250 mL CH2Cl2 cooled to −78° C. was added dropwise via syringe BBr3 (9.8 mL; 0.104 mol). After 1 h at −78° C. the reaction was stirred for 4 h in an ice-water bath. The reaction mixture was recooled to −78° C. and the reaction quenched aqueous NaHCO3 then warmed to rt and the organic phase washed with water, saturated NaHCO3 and brine. The organic phase was dried (MgSO4) and the solvent evaporated to afford 1.4 g of ethyl 3-hydroxy-4-methylphenylacetate (5a).

Workup

  1. customwas recooled to −78° C.
  2. customthe reaction quenched aqueous NaHCO3
  3. temperaturethen warmed to rt
  4. washthe organic phase washed with water, saturated NaHCO3 and brine
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-8b01cabdcdb2463cb7a27ad655da719a
Source dataset
uspto-grants-2007_04
Patent number
US07208509B2

Reaction notes

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