tert-Butyl acetate → Methyl 2-(4-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate

HRID 514145Notes

Reaction equation

HRID 514145 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[C:4]([CH:19]([OH:24])[C:20]([O:22][CH3:23])=[O:21])[C:3]=1[CH3:25].[C:26](OC(C)=O)([CH3:29])([CH3:28])[CH3:27].C([O-])(O)=O.[Na+]>Cl(O)(=O)(=O)=O>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=2)=[C:4]([CH:19]([O:24][C:26]([CH3:29])([CH3:28])[CH3:27])[C:20]([O:22][CH3:23])=[O:21])[C:3]=1[CH3:25]

Participants

5

Reactant 3

HCID 10908tert-Butyl acetateHCID 516892Sodium BicarbonateHCID 67126228Methyl 2-(4-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-hydroxyacetate

Product 1

HCID 67126267Methyl 2-(4-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate

Reagents, catalysts & solvents 1

HCID 24247Perchloric AcidCatalyst

Procedure

Methyl 2-(4-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-hydroxyacetate (298 mg, 0.71 mmol) was dissolved in t-BuOAc (18.0 mL, 134 mmol) and 7 drops of perchloric acid were added. The reaction was monitored by HPLC and TLC for progress. After 4.5 hours, the mixture was added to icy saturated NaHCO3 and stirred for 10-15 minutes. This mixture was extracted with EtOAc, extracts dried with sodium sulfate and concentrated in vacuo. Purification on silica gel using EtOAc in hexanes gave desired product as well as some starting material. 1H-NMR: (400 MHz, CDCl3): δ 8.39 (d, J=8.8 Hz, 1H); 7.57-7.48 (m, 3H); 7.45-7.42 (m, 1H); 7.35-7.31 (m, 1H); 7.28-7.18 (m, 2H); 5.20 (s, 1H); 3.70 (s, 3H); 2.72 (s, 3H); 0.99 (s, 9H).

Workup

  1. extractionThis mixture was extracted with EtOAc
  2. dry with materialextracts dried with sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customPurification on silica gel

Sources & evidence

ORD record
ord-2c7e6887bdbd4d6199dbc0904000809d
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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