Benzyl Bromide → Methyl 5-(4-morpholinylsulfonyl)-2-[(phenylmethyl)oxy]benzoate

HRID 1623687Notes

Reaction equation

HRID 1623687 reaction equation
C([O-])([O-])=O.[K+].[K+].[OH:7][C:8]1[CH:17]=[CH:16][C:15]([S:18]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)(=[O:20])=[O:19])=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11].Br[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CC(C)=O>[N:21]1([S:18]([C:15]2[CH:16]=[CH:17][C:8]([O:7][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[C:9]([CH:14]=2)[C:10]([O:12][CH3:13])=[O:11])(=[O:20])=[O:19])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 14266921Methyl 2-hydroxy-5-(4-morpholinylsulfonyl)benzoate

Product 1

HCID 67107150Methyl 5-(4-morpholinylsulfonyl)-2-[(phenylmethyl)oxy]benzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

K2CO3 (138 mg, 1.00 mmol) was added to a stirred solution of methyl 2-hydroxy-5-(4-morpholinylsulfonyl)benzoate (may be prepared as described in Description 64; 300 mg, 1.00 mmol) in acetone (20 ml), followed by the addition of (bromomethyl)benzene (170 mg, 1.00 mmol). The mixture was heated to reflux for 16 h, and then cooled to room temperature. The mixture was filtered, and the filtrate was concentrated to yield the title compound as a colourless oil. 380 mg.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 16 h
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-677c4b8232614d7baf7e1953cb48ad73
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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