Bromine → 5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-1-bromo-2-hydroxynaphthalene-3-carboxylic acid

HRID 1636549Notes

Reaction equation

HRID 1636549 reaction equation
[CH3:1][C:2]1([CH3:18])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([OH:14])[C:5]([C:15]([OH:17])=[O:16])=[CH:4][C:3]1=2.[Br:19]Br>CC(O)=O>[Br:19][C:7]1[C:8]2[C:9]([CH3:12])([CH3:13])[CH2:10][CH2:11][C:2]([CH3:18])([CH3:1])[C:3]=2[CH:4]=[C:5]([C:15]([OH:17])=[O:16])[C:6]=1[OH:14]

Participants

4

Reactant 2

HCID 24408BromineHCID 106820163-Hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid2×

Product 1

HCID 106398845,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-1-bromo-2-hydroxynaphthalene-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-Hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl acid (Compound L, 155 mg, 0.62 mmol) was dissolved in 1 ml of HOAc. To this solution was added Br2 (0.033 ml, 0.62 mmol). The reaction mixture was left at room temperature for over night. A stream of air was passed through the reaction mixture to remove the unreacted Br2. The remaining solid was dissolved in small amount of THF and purified by column chromatography (ethyl acetate/hexane 1/1) to yield the desired product as a cream colored solid.

Workup

  1. waitThe reaction mixture was left at room temperature for over night
  2. customto remove the unreacted Br2
  3. dissolutionThe remaining solid was dissolved in small amount of THF
  4. custompurified by column chromatography (ethyl acetate/hexane 1/1)

Sources & evidence

ORD record
ord-8c31886dbb8a4521ba493eb0f296661c
Source dataset
uspto-grants-2000_03
Patent number
US06034244

Reaction notes

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