Triethylamine → t-Butyl 2-(2-bromo-4-((4-fluorophenylsulfonamido)methyl)phenoxy)acetate

HRID 68590Notes

Reaction equation

HRID 68590 reaction equation
[NH2:1][CH2:2][C:3]1[CH:17]=[CH:16][C:6]([O:7][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[C:5]([Br:18])[CH:4]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.CCN(CC)CC>C(Cl)Cl>[Br:18][C:5]1[CH:4]=[C:3]([CH2:2][NH:1][S:26]([C:23]2[CH:24]=[CH:25][C:20]([F:19])=[CH:21][CH:22]=2)(=[O:28])=[O:27])[CH:17]=[CH:16][C:6]=1[O:7][CH2:8][C:9]([O:11][C:12]([CH3:14])([CH3:15])[CH3:13])=[O:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 66868573t-Butyl 2-(4-(aminomethyl)-2-bromophenoxy)acetate

Product 1

HCID 66869000t-Butyl 2-(2-bromo-4-((4-fluorophenylsulfonamido)methyl)phenoxy)acetateYield 48.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of t-butyl 2-(4-(aminomethyl)-2-bromophenoxy)acetate (6) (88 mg, 1 eq, 0.28 mmol) in DCM (15 mL) was added 4-fluoro-benzenesulfonyl chloride (65 mg, 0.33 mmol, 1.2 eq) and Et3N (56 mg, 0.56 mmol, 2 eq). The mixture was stirred at room temperature for 2 h, filtered, concentrated in vacuo and purified by preparative TLC to give 64 mg (48%) of t-butyl 2-(2-bromo-4-((4-fluorophenylsulfonamido)methyl)phenoxy)acetate (7).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. custompurified by preparative TLC

Sources & evidence

ORD record
ord-35a47df492b94de7b5f59fd14b3367bd
Source dataset
uspto-grants-2014_09
Patent number
US08822467B2

Reaction notes

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