Hexamethylenetetramine → 3-Bromo-2-fluoro-4-methoxybenzaldehyde

HRID 1632099Notes

Reaction equation

HRID 1632099 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][CH3:10].C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:23](O)=[O:24]>>[Br:1][C:2]1[C:7]([F:8])=[C:6]([CH:5]=[CH:4][C:3]=1[O:9][CH3:10])[CH:23]=[O:24]

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acid2×HCID 27793182-Bromo-3-fluoroanisole

Product 1

HCID 577037373-Bromo-2-fluoro-4-methoxybenzaldehyde

Conditions

Temperature
80 °C

Procedure

A solution of 2-bromo-3-fluoroanisol (5.00 g, 24.4 mmol) in trifluoroacetic acid (25 mL) was heated to 80° C. and then a solution of hexamethylenetetramine (6.83 g, 48.8 mmol) in trifluoroacetic acid (25 mL) was added dropwise over 1.5 h. Upon completion of the addition, the reaction was stirred at 80° C. for 1 h under nitrogen. The excess trifluoroacetic acid was removed under vacuum, and the pH was adjusted to 7.5-8.0 by addition of saturated aqueous potassium carbonate (˜100 mL). The white solid that formed was filtered to give I-30 which was used without additional purification.

Workup

  1. additionUpon completion of the addition
  2. customThe excess trifluoroacetic acid was removed under vacuum
  3. additionthe pH was adjusted to 7.5-8.0 by addition of saturated aqueous potassium carbonate (˜100 mL)
  4. customThe white solid that formed
  5. filtrationwas filtered
  6. customto give I-30 which
  7. customwas used without additional purification

Sources & evidence

ORD record
ord-54e1bd8c1c9d41d4be1181aa804c8072
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

Loading…