5-Bromoacetyl-2-hydroxybenzaldehyde Chemical Properties

Melting point:

117-118 °C(Solv: dichloromethane (75-09-2))

Boiling point:

368.3±32.0 °C(Predicted)

Density 

1.685±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly, Heated)

form 

Solid

pka

5.93±0.20(Predicted)

color 

Yellow to Dark Yellow

Stability:

Moisture Sensitive

InChI

InChI=1S/C9H7BrO3/c10-4-9(13)6-1-2-8(12)7(3-6)5-11/h1-3,5,12H,4H2

InChIKey

LPSGRBXPXIPMPF-UHFFFAOYSA-N

SMILES

C(=O)C1=CC(C(CBr)=O)=CC=C1O

5-Bromoacetyl-2-hydroxybenzaldehyde Usage And Synthesis

Chemical Properties

Brown Solid

Uses

Intermediate in the preparation of Salmeterol (S090100).

Synthesis

To a suspension of aluminum chloride (4 mole equivalents) in dichloromethane (10 volumes), bromoacetyl bromide (1.2 mole equivalents) was added slowly and dropwise at 100 °C, and the temperature of the reaction system was subsequently adjusted to 30 °C. The reaction mixture was stirred continuously for 1 hour, and then 2-hydroxybenzaldehyde (1 mole equivalent) was added dropwise in dichloromethane. The reaction mixture was stirred continuously at this temperature for 1 h. Then a dichloromethane solution of 2-hydroxybenzaldehyde (1 mole equivalent) was added dropwise. The reaction mixture was stirred at 35-40 °C for 12-15 hours, followed by quenching the reaction with water at 0-50 °C. The organic layer (dichloromethane layer) was separated and the solvent was removed by distillation. To the residue n-heptane was added and stirred for 15 minutes. The resulting slurry was filtered and the wet filter cake was washed with n-heptane (2 vol). The wet filter cake was dried to constant weight at 50 °C to give the intermediate 5-bromoacetyl-2-hydroxybenzaldehyde (2a). Yield: 55% (w/w); HPLC purity: 97-99

References

[1] Angewandte Chemie - International Edition, 2016, vol. 55, # 13, p. 4194 - 4198
[2] Angew. Chem., 2016, vol. 128, # 13, p. 4266 - 4270,5
[3] Tetrahedron Asymmetry, 2008, vol. 19, # 15, p. 1824 - 1828
[4] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 5, p. 1548 - 1552
[5] Chemical Communications, 2018, vol. 54, # 25, p. 3106 - 3109

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