Sulfuric Acid → 7-Bromo-3-methylnaphthalen-1-ol

HRID 926202

Reaction equation

HRID 926202 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([CH3:16])=[CH:10][C:11]([O:13]CC)=O)=[CH:4][CH:3]=1.OS(O)(=O)=O>>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([CH:8]=[C:9]([CH3:16])[CH:10]=[C:11]2[OH:13])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 67126147Ethyl 4-(4-bromophenyl)-3-methylbut-2-enoate

Product 1

HCID 671262827-Bromo-3-methylnaphthalen-1-ol

Conditions

Temperature
50 °C

Procedure

A flask containing the crude ethyl 4-(4-bromophenyl)-3-methylbut-2-enoate from above (˜30 grams) was treated with concentrated H2SO4 (120 mL) and warmed to 50° C. for 2.5 h. The reaction was poured onto ˜500 mL of crushed ice. Once the ice had thawed, the brown suspension was extracted with two portions of EtOAc (500 mL and 100 mL, respectively). The two extracts were combined, washed with saturated NaHCO3, dried (MgSO4), filtered, and concentrated to ˜55 mL. The residue was treated with DCM and loaded onto a silica gel column and purified by flash chromatography (ethyl acetate/hexanes) giving the desired product. 1H NMR (400 MHz, CDCl3) δ 8.29 (d, J=1.9 Hz, 1H), 7.57 (d, J=8.6 Hz, 1H), 7.50 (dd, J=8.6, 2.0 Hz, 1H), 7.17 (s, 1H), 6.67 (s, 1H), 2.42 (s, 3H).

Workup

  1. extractionthe brown suspension was extracted with two portions of EtOAc (500 mL and 100 mL
  2. washwashed with saturated NaHCO3
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated to ˜55 mL
  6. additionThe residue was treated with DCM
  7. custompurified by flash chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-8fd3423e43d84f62a31b1cf6b85b3afa
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Linked notes

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