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

HRID 1095077Notes

Reaction equation

HRID 1095077 reaction equation
[Cl:1][C:2]1[C:3]([F:12])=[C:4]([C:7]([O:10]C)=[CH:8][CH:9]=1)[CH:5]=[O:6].B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[C:3]([F:12])=[C:4]([C:7]([OH:10])=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 221397073-Chloro-2-fluoro-6-methoxybenzaldehyde

Product 1

HCID 589347903-Chloro-2-fluoro-6-hydroxybenzaldehydeYield 22.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-chloro-2-fluoro-6-methoxy-benzaldehyde (10 g, 53.2 mmol,) in dichloromethane (200 mL) at −78° C. was added a dichloromethane solution (1 M) of BBr3 (159 mL, 159 mmol) dropwise. The mixture was gradually warmed to room temperature and stirred for 1 h, then quenched with water. The mixture was extracted with dichloromethane three times. The organic layer were combined, washed with brine, dried over MgSO4, concentrated to give a residue. The reside was triturated with dichloromethane and hexanes to afford 3-chloro-2-fluoro-6-hydroxy-benzaldehyde as a brown solid (Yield: 2.07 g, 22%)

Workup

  1. customquenched with water
  2. extractionThe mixture was extracted with dichloromethane three times
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto give a residue
  7. customThe reside was triturated with dichloromethane and hexanes

Sources & evidence

ORD record
ord-89e76eaa207b45609c87dda350f7d0f9
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

Loading…