Boron tribromide → 5-Chloro-2,3-dihydroxybenzaldehyde

HRID 2367996Notes

Reaction equation

HRID 2367996 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:11]C)[C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 51510865-Chloro-2-hydroxy-3-methoxybenzaldehyde

Product 1

HCID 219248625-Chloro-2,3-dihydroxybenzaldehydeYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 5-chloro-2-hydroxy-3-methoxy-benzaldehyde (7 g, 37.5 mmol) in anhydrous CH2Cl2 (200 mL) at 0° C. was added a solution of BBr3 in CH2Cl2 (1 M, 93.7 mL, 93.7 mmol) and the reaction mixture was stirred overnight at room temperature. The solution was diluted with CH2Cl2 (200 mL), washed with water, brine, dried over Na2SO4, filtered and concentrated under reduced pressure generating the title compound (6.2 g, 36.0 mmol, 96%) as a light yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 11.02 (s, 1H), 9.83 (s, 1H), 7.18 (s, 1H), 7.14 (d, J=2.3 Hz, 1H), 5.71 (s, 1H).

Workup

  1. washwashed with water, brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3071076a3c9c473c97411d1d8c02b0bf
Source dataset
uspto-grants-2014_04
Patent number
US08703742B2

Reaction notes

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