Hydrochloric Acid → 3-Bromo-5-tert-butyl-2-hydroxybenzaldehyde

HRID 1480607Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[OH:12].C1N2CN3CN(C2)CN1C3.Cl.FC(F)(F)[C:26](O)=[O:27]>>[Br:1][C:2]1[C:3]([OH:12])=[C:4]([CH:5]=[C:6]([C:8]([CH3:9])([CH3:11])[CH3:10])[CH:7]=1)[CH:26]=[O:27]

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 4101Hexamethylenetetramine

HCID 6422Trifluoroacetic acid

HCID 751472-Bromo-4-tert-butylphenol2×

Product 1

HCID 71720963-Bromo-5-tert-butyl-2-hydroxybenzaldehydeYield 88%

Conditions

Temperature: 90 °C

Procedure

A mixture of 2-bromo-4-(tert-butyl)phenol [Intermediate 1, Step 1] (6.87 g, 30 mmol) and hexamethylenetetramine (20 g, 143 mmol) in trifluoroacetic acid (60 mL) was heated at 90° C. under nitrogen for 22 hours. The hot reaction mixture was poured into 1M aqueous hydrochloric acid (200 mL) and the mixture stirred vigorously for 6 hours. The resulting suspension was filtered to give 3-bromo-5-(tert-butyl)-2-hydroxybenzaldehyde (6.79 g, 88% yield) as a yellow solid.

Workup

filtrationThe resulting suspension was filtered

Sources & evidence

ORD record: ord-8f28836fb4fd412e899e6f2543f5c314
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409893B2

Reaction notes

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