1-Bromo-4-fluorobutane → HCID 67436058, compound

HRID 1662981Notes

Reaction equation

HRID 1662981 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][N:5]([S:15]([C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1)(=[O:17])=[O:16])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:33][CH2:34][CH2:35][CH2:36][F:37]>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:25])[CH2:4][N:5]([S:15]([C:18]1[CH:19]=[CH:20][C:21]([O:24][CH2:33][CH2:34][CH2:35][CH2:36][F:37])=[CH:22][CH:23]=1)(=[O:17])=[O:16])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 100221-Bromo-4-fluorobutaneHCID 11430Potassium CarbonateHCID 67435286[(4-Hydroxy-benzenesulfonyl)-(4-methoxy-benzyl)amino]-acetic acid methyl ester

Product 1

HCID 67436058HCID 67436058, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 1 g (2.74 mmol) of [(4-hydroxy-benzenesulfonyl)-(4-methoxy-benzyl)amino]-acetic acid methyl ester and 1.14 g (8.22 mmol) of K2CO3 in 8 ml of DMF, 0.59 ml (5.47 mmol) of 1-bromo-4-fluorobutane is added dropwise at r.t. After stirring for 18 h at r.t., the reaction mixture is diluted with H2O and extracted with AcOEt. The combined extracts are washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (AcOEt:n-hexane=3:1) to give {[4-(4-fluorobutoxy)-benzenesulfonyl](4-methoxy-benzyl)-amino}-acetic acid methyl ester; NMR (CDCl3): 1.86-1.96 (m, 4H), 3.57 (s, 3H), 3.79 (s, 3H), 3.90 (s, 2H), 4.08 (t, 2H, J=6.04 Hz), 4.39 (s, 2H), 4.46 (t, 1H, J=6.04 Hz), 4.55-4.65 (m, 1H), 6.83 (d, 2H, J=8.56 Hz), 6.97 (d, 2H, J=9.08 Hz), 7.15 (d, 2H, J=8.56 Hz), 7.82 (d, 2H, J=9.08 Hz).

Workup

  1. additionis added dropwise at r.t
  2. extractionextracted with AcOEt
  3. washThe combined extracts are washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by column chromatography on silica gel (AcOEt:n-hexane=3:1)

Sources & evidence

ORD record
ord-e6d73a7fc56441cc9623d82a9fb4a2c7
Source dataset
uspto-grants-2011_10
Patent number
US08034810B2

Reaction notes

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