Methyl 4-(bromomethyl)benzoate → HCID 59756929, compound

HRID 1880595Notes

Reaction equation

HRID 1880595 reaction equation
CC(C)([O-])C.[Na+].[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14](=[O:33])[CH2:15][C:16]1[CH:17]=[C:18]([C:22]2[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=2)[CH:19]=[CH:20][CH:21]=1.[CH3:34][O:35][C:36](=[O:45])[C:37]1[CH:42]=[CH:41][C:40]([CH2:43]Br)=[CH:39][CH:38]=1>C1COCC1>[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14](=[O:33])[CH:15]([C:16]1[CH:17]=[C:18]([C:22]2[CH:27]=[CH:26][C:25]([O:28][C:29]([F:31])([F:32])[F:30])=[CH:24][CH:23]=2)[CH:19]=[CH:20][CH:21]=1)[CH2:43][C:40]1[CH:41]=[CH:42][C:37]([C:36]([O:35][CH3:34])=[O:45])=[CH:38][CH:39]=1

Participants

5

Reactant 3

HCID 256687Methyl 4-(bromomethyl)benzoateHCID 23676156Sodium t-butoxideHCID 69307037HCID 69307037, compound

Product 1

HCID 59756929HCID 59756929, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Sodium t-butoxide (67 mg, 0.70 mmol) was added all at once to a THF solution (4 mL) containing the intermediate from Step B (250 mg, 0.668 mmol) stirred at −78° C. After 2 minutes 4-bromomethyl-benzoic acid methyl ester (161 mg, 0.70 mmol) was added all at once. 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 7.92-7.90 (m, 2H); 7.79-7.75 (m, 1H); 7.51-7.49 (m, 2H); 7.47-7.32 (m, 4H); 7.30-7.27 (m, 2H); 7.24-7.19 (m, 3H); 7.17-7.15 (m, 1H); 7.05 (dd, J=8.3, 11.3 Hz, 1H); 4.88 (t, J=7.4 Hz, 1H); 3.91 (s, 3H); 3.68 (dd, J=7.1, 13.7 Hz, 1H); 3.17 (dd, J=7.6, 13.7 Hz, 1H). LCMS1 4.40 min. (M+H)− 523

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-485f1ac8a648418798d317d35d79adce
Source dataset
uspto-grants-2012_11
Patent number
US08318760B2

Reaction notes

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