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

HRID 1854170Notes

Reaction equation

HRID 1854170 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].BrC1C2[O:22][CH2:21]N(C(C)(C)C)CC=2C=C(C(C)(C)C)C=1.C1N2CN3CN(C2)CN1C3.Cl>FC(F)(F)C(O)=O>[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:21]=[O:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4101HexamethylenetetramineHCID 751472-Bromo-4-tert-butylphenolHCID 867185598-bromo-3,6-di-tert-butyl-3,4-dihydro-2H-benzo[e][1,3]oxazine

Product 1

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

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

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

  1. filtrationThe resulting suspension was filtered

Sources & evidence

ORD record
ord-a08a702917924f8096b1692cacea46b2
Source dataset
uspto-grants-2015_02
Patent number
US08962657B2

Reaction notes

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