3-bromo-5-tert-butyl-4-hydroxybenzaldehyde

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 3-tert-butyl-4-hydroxybenzaldehyde (3 gm) in acetic acid (30 ml) was added dropwise bromine (1.5 ml). The mixture was stirred at 25° for 3 hours and the solvent removed in vacuo. Recrystallisation of the residue from aqueous ethanol gave 3-bromo-5-tert-butyl-4-hydroxybenzaldehyde (3.2 gm) m.p. 126°. the solvent removed in vacuo Recrystallisation of the residue from aqueous ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 3-tert-butyl-4-hydroxybenzaldehyde (3 gm) in acetic acid (30 ml) was added dropwise bromine (1.5 ml). The mixture was stirred at 25° for 3 hours and the solvent removed in vacuo. Recrystallisation of the residue from aqueous ethanol gave 3-bromo-5-tert-butyl-4-hydroxybenzaldehyde (3.2 gm) m.p. 126°. the solvent removed in vacuo Recrystallisation of the residue from aqueous ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a similar manner as described in Example 2 reaction of 3-bromo-5-tert-butyl-4-hydroxybenzaldehyde and malononitrile gave 3-bromo-5-tert-butyl-4-hydroxybenzylidenemalononitrile as pale yellow needles from alcohol m.p. 185°.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5-Chloro-2-oxindole (167 mg, 1 mmol) was condensed with 3-bromo-5-tert-butyl-4-hydroxybenzaldehyde (308.5 mg, 1.2 mmol) using method B to give 329 mg (81%) of 3-(3-bromo-5-tert-butyl-4-hydroxybenzylidene)-5-chloro-1,3-dihydroindol-2-one as a mixture of isomers.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 3-tert-butyl-4-hydroxybenzaldehyde (3 gm) in acetic acid (30 ml) was added dropwise bromine (1.5 ml). The mixture was stirred at 25° for 3 hours and the solvent removed in vacuo. Recrystallisation of the residue from aqueous ethanol gave 3-bromo-5-tert-butyl-4-hydroxybenzaldehyde (3.2 gm) m.p. 126°. the solvent removed in vacuo Recrystallisation of the residue from aqueous ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a similar manner as described in Example 2 reaction of 3-bromo-5-tert-butyl-4-hydroxybenzaldehyde and malononitrile gave 3-bromo-5-tert-butyl-4-hydroxybenzylidenemalononitrile as pale yellow needles from alcohol m.p. 185°.