Ethyl 4-(3-bromophenyl)-3-methylbut-2-enoate → 6-Bromo-3-methylnaphthalen-1-ol

HRID 926181Notes

Reaction equation

HRID 926181 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([CH3:16])=[CH:10][C:11]([O:13]CC)=O)[CH:5]=[CH:6][CH:7]=1>S(=O)(=O)(O)O.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[C:11]([OH:13])=[CH:10][C:9]([CH3:16])=[CH:8]2

Participants

4

Reactant 1

HCID 123263883Ethyl 4-(3-bromophenyl)-3-methylbut-2-enoate

Product 1

HCID 708356316-Bromo-3-methylnaphthalen-1-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of ethyl 4-(3-bromophenyl)-3-methylbut-2-enoate (8.07 g, 28.5 mmol) in concentrated sulfuric acid (20 mL) was stirred at 60° C. for 90 minutes. The reaction mixture was poured onto ice and diluted with water and extracted with ethyl acetate. The organic layer was concentrated and purified by flash column chromatography (silica gel, ethyl acetate/hexanes) to give the desired compound. 1H-NMR: 400 MHz, (CDCl3) δ: 7.98 (d, J=10.4 Hz, 1H), 7.83 (s, 1H), 7.43 (d, J=7.2 Hz, 1H), 7.08 (s, 1H), 6.67 (s, 1H), 2.42 (s, 3H). LCMS-ESI− (m/z): [M−H]− calcd for C11H9BrO: 236.09. Found: 236.9.

Workup

  1. additionThe reaction mixture was poured onto ice
  2. extractionextracted with ethyl acetate
  3. concentrationThe organic layer was concentrated
  4. custompurified by flash column chromatography (silica gel, ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-41dbf3ffd930456fa1b304ce134b9f38
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

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