Boron tribromide → 2,4-Difluoro-3-hydroxybenzaldehyde

HRID 1184545Notes

Reaction equation

HRID 1184545 reaction equation
B(Br)(Br)Br.[F:5][C:6]1[C:13]([O:14]C)=[C:12]([F:16])[CH:11]=[CH:10][C:7]=1[CH:8]=[O:9]>C(Cl)Cl.C1COCC1.O>[F:5][C:6]1[C:13]([OH:14])=[C:12]([F:16])[CH:11]=[CH:10][C:7]=1[CH:8]=[O:9]

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 37202372,4-Difluoro-3-methoxybenzaldehyde

Product 1

HCID 5939092,4-Difluoro-3-hydroxybenzaldehydeYield 98%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
-10 °C

Procedure

1M BBr3 in DCM (2.179 ml) was added dropwise in about 30 min. to a stirred solution of 2,4-difluoro-3-methoxybenzaldehyde (0.25 g, 1.452 mmol) in DCM, cooled at −10° C. and under nitrogen atmosphere The solution was stirred for 4 hrs at RT and then diluted with a mixture of THF/H2O (9/1) and heated for 30 min. at 80° C. The solvent was removed and the residue was partitioned between 10N NaOH and Et2O. The aqueous layer was acidified with 10 N HCl and extracted with Et2O/EtOAc (2/1). Organic layers were dried over sodium sulphate and evaporated to give 2,4-difluoro-3-hydroxybenzaldehyde (225 mg) as pale brown powder.

Workup

  1. temperatureheated for 30 min. at 80° C
  2. customThe solvent was removed
  3. customthe residue was partitioned between 10N NaOH and Et2O
  4. extractionextracted with Et2O/EtOAc (2/1)
  5. dry with materialOrganic layers were dried over sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-dd23c676d49047778783147028ad0e6e
Source dataset
uspto-grants-2014_03
Patent number
US08669261B2

Reaction notes

Loading…