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

HRID 1095073Notes

Reaction equation

HRID 1095073 reaction equation
[Br: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>[Br: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 577432213-Bromo-2-fluoro-6-methoxybenzaldehyde

Product 1

HCID 577433543-Bromo-2-fluoro-6-hydroxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-bromo-2-fluoro-6-methoxy-benzaldehyde (9.8 g, 42.06 mmol,) in dichloromethane (200 mL) at −50° C. was added a dichloromethane solution (1 M) of BBr3 (126 mL, 126 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 3-bromo-2-fluoro-6-hydroxy-benzaldehyde as a off white solid (Yield: 9 g, 98%)

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

Sources & evidence

ORD record
ord-98dff4518a7a4e45b9e6d9f2f8216c94
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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