Boron tribromide → 3-Chloro-4-methoxysalicylaldehyde

HRID 1263286Notes

Reaction equation

HRID 1263286 reaction equation
[Cl:1][C:2]1[C:3]([O:12]C)=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[C:3]([OH:12])=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 133437053-Chloro-2,4-dimethoxybenzaldehyde

Product 1

HCID 133437063-Chloro-4-methoxysalicylaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 72.0 g. (0.359 mol) of (13h) in 450 ml. of CH2Cl2 at -50° C. under N2 was added dropwise 90.0 g. (0.359 mol) of BBr3. After the addition was complete, the reaction mixture was warmed to 0° C. and stirred for 1 hour. The reaction mixture was then poured into 500 ml. of ice-water and extracted with EtOAc. The organic solution was washed with aqueous NaCl and dried over Na2SO4. Evaporation of the EtOAc gave a residue that was rapidly passed through a silica gel column eluting with an EtOAc/CH2Cl2 mixture. This afforded 49.5 g. of (14h), m.p. 114°-117° C. Analysis (C8H7ClO3) C,H.

Workup

  1. additionAfter the addition
  2. additionThe reaction mixture was then poured into 500 ml
  3. extractionof ice-water and extracted with EtOAc
  4. washThe organic solution was washed with aqueous NaCl
  5. dry with materialdried over Na2SO4
  6. customEvaporation of the EtOAc
  7. customgave a residue that
  8. washeluting with an EtOAc/CH2Cl2 mixture

Sources & evidence

ORD record
ord-092dd87775ad4c868b7578f3ef67bd3f
Source dataset
uspto-grants-1984_06
Patent number
US04456612

Reaction notes

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