Methyl 4-(bromomethyl)benzoate → HCID 69311681, compound

HRID 1880593Notes

Reaction equation

HRID 1880593 reaction equation
CC(C)([O-])C.[Na+].[Cl:7][C:8]1[CH:9]=[C:10]([CH2:14][C:15](=[O:17])[CH3:16])[CH:11]=[CH:12][CH:13]=1.[CH3:18][O:19][C:20](=[O:29])[C:21]1[CH:26]=[CH:25][C:24]([CH2:27]Br)=[CH:23][CH:22]=1>C1COCC1>[Cl:7][C:8]1[CH:9]=[C:10]([CH:14]([C:15](=[O:17])[CH3:16])[CH2:27][C:24]2[CH:25]=[CH:26][C:21]([C:20]([O:19][CH3:18])=[O:29])=[CH:22][CH:23]=2)[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 256687Methyl 4-(bromomethyl)benzoateHCID 27340971-(3-Chlorophenyl)propan-2-oneHCID 23676156Sodium t-butoxide

Product 1

HCID 69311681HCID 69311681, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Sodium t-butoxide (0.60 g, 6.34 mmol) was added all at once to a THF solution (10 mL) of 1-(3-chloro-phenyl)-propan-2-one (1.08 g, 6.40 mmol) stirred at −78° C. After 3 minutes 4-bromomethyl-benzoic acid methyl ester (1.54 g, 6.72 mmol) was added all at once and the reaction solution was allowed to warm to room temperature. After stirring for 1 hour the reaction solution was partitioned between aqueous 1N HCl and ethyl acetate. The organic phase was washed with brine and dried over MgSO4. The solution was filtered, concentrated and the residue purified by silica gel chromatography using a hexanes/ethyl acetate gradient to give the title compound. 1H NMR (500 MHz, CDCl3): δ 7.91 (d, J=8.2 Hz, 2H); 7.29-7.25 (m, 2H); 7.20 (s, 1H); 7.13 (d, J=8.2 Hz, 2H); 7.07-7.03 (m, 1H); 3.91 (broad s, 4H); 3.47 (dd, J=7.2, 13.8 Hz, 1H); 2.96 (dd, J=7.6, 13.8 Hz, 1H); 2.07 (s, 3H). LCMS1 3.66 min. (M+H)=317.

Workup

  1. temperatureto warm to room temperature
  2. stirringAfter stirring for 1 hour the reaction solution
  3. customwas partitioned between aqueous 1N HCl and ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationThe solution was filtered
  7. concentrationconcentrated
  8. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-1fc9c5804dc34f84835b3f27af1a47cc
Source dataset
uspto-grants-2012_11
Patent number
US08318760B2

Reaction notes

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