Benzyl Bromide → Methyl 5-(dimethylsulfamoyl)-2-phenylmethoxybenzoate

HRID 1623684Notes

Reaction equation

HRID 1623684 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH3:7][N:8]([CH3:23])[S:9]([C:12]1[CH:13]=[CH:14][C:15]([OH:22])=[C:16]([CH:21]=1)[C:17]([O:19][CH3:20])=[O:18])(=[O:11])=[O:10].Br[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CC(C)=O>[CH3:23][N:8]([CH3:7])[S:9]([C:12]1[CH:13]=[CH:14][C:15]([O:22][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:16]([CH:21]=1)[C:17]([O:19][CH3:20])=[O:18])(=[O:10])=[O:11]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 14266919Methyl 5-[(dimethylamino)sulfonyl]-2-hydroxybenzoate

Product 1

HCID 67106778Methyl 5-(dimethylsulfamoyl)-2-phenylmethoxybenzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

K2CO3 (139 mg, 1.00 mmol) was added to a stirred solution of methyl 5-[(dimethylamino)sulfonyl]-2-hydroxybenzoate (may be prepared as described in Description 61; 260 mg, 1.00 mmol) in acetone (30 ml), followed by the addition of (bromomethyl)benzene (172 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. 300 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-f8d7f2da46784785af28919ede87d333
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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