Trifluoroacetic acid → 5-(2,6-Dibromo-3-methyl-4-nitrophenoxy)-2-hydroxy-3-isopropylbenzaldehyde

HRID 1392553Notes

Reaction equation

[Br:1][C:2]1[C:18]([CH3:19])=[C:17]([N+:20]([O-:22])=[O:21])[CH:16]=[C:15]([Br:23])[C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH:12]([CH3:14])[CH3:13])[CH:6]=1.[C:24](O)(C(F)(F)F)=[O:25]>Cl>[Br:1][C:2]1[C:18]([CH3:19])=[C:17]([N+:20]([O-:22])=[O:21])[CH:16]=[C:15]([Br:23])[C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH:12]([CH3:14])[CH3:13])[C:8]([OH:11])=[C:9]([CH:10]=1)[CH:24]=[O:25]

Participants

Conditions

Temperature: 95 °C

Procedure

Hexamethylentetramine (197 mg, 1.4 mmol) was added to a solution of compound 4-(2,6-dibromo-3-methyl-4-nitrophenoxy)-2-isopropylphenol of Part 8C (250 mg, 0.56 mmol) and TFA (5 mL). The resulting reaction mixture was stirred for 16 hours at 95° C. The reaction mixture was cooled to room temperature and 1N HCl (10 mL) was added. After another hour of stirring, the reaction mixture was extracted with EtOAc (3×30 mL), the combined organic phases washed by 1N HCl (15 mL), H2O (20 mL) and brine (20 mL). After drying over Na2SO4, concentration and filtration through a pad of silica, 210 mg (79%) of 5-(2,6-dibromo-3-methyl-4-nitrophenoxy)-2-hydroxy-3-isopropylbenzaldehyde was obtained as a light yellow solid.

Workup

customThe resulting reaction mixture
temperatureThe reaction mixture was cooled to room temperature
stirringAfter another hour of stirring
extractionthe reaction mixture was extracted with EtOAc (3×30 mL)
washthe combined organic phases washed by 1N HCl (15 mL), H2O (20 mL) and brine (20 mL)
dry with materialAfter drying over Na2SO4, concentration and filtration through a pad of silica

Sources & evidence

ORD record: ord-abd88c2a644a4bd49b99f98de6862a2f
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07342127B2

Reaction notes

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