Boron tribromide → 6-Bromo-2-fluoro-3-hydroxybenzaldehyde

HRID 2284476Notes

Reaction equation

HRID 2284476 reaction equation
[Br:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([F:10])[C:5]([O:11]C)=[CH:4][CH:3]=1.B(Br)(Br)Br>ClCCl>[Br:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([F:10])[C:5]([OH:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 231579156-Bromo-2-fluoro-3-methoxybenzaldehyde

Product 1

HCID 534387996-Bromo-2-fluoro-3-hydroxybenzaldehydeYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-bromo-2-fluoro-3-methoxybenzaldehyde (2.0 g, 8.6 mmol) in dichloromethane (43 mL) under a nitrogen balloon was cooled to −78° C. in an acetone dry ice bath. Boron tribromide (1 M in dichloromethane, 9.5 mL) was added dropwise under nitrogen atmosphere. The reaction was stirred at room temperature overnight. The flask was then put on an ice water bath and the excess boron tribromide was quenched with ice chips. Water was added and the solution was extracted with dichloromethane. The aqueous layer was extracted twice with dichloromethane. The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate, and filtered. The solvent was removed under reduced pressure to give 6-bromo-2-fluoro-3-hydroxybenzaldehyde (1.61 g, 86%).

Workup

  1. customThe flask was then put on an ice water bath
  2. customthe excess boron tribromide was quenched with ice chips
  3. additionWater was added
  4. extractionthe solution was extracted with dichloromethane
  5. extractionThe aqueous layer was extracted twice with dichloromethane
  6. washwashed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0fd99c23137448fdbf0e636542768240
Source dataset
uspto-grants-2015_09
Patent number
US09145429B2

Reaction notes

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