Methanesulfonyl chloride → N-(2-Fluoro-4-hydroxyphenyl)methanesulfonamide

HRID 133782Notes

Reaction equation

HRID 133782 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].[CH3:10][S:11](Cl)(=[O:13])=[O:12]>N1C=CC=CC=1>[F:9][C:3]1[CH:4]=[C:5]([OH:8])[CH:6]=[CH:7][C:2]=1[NH:1][S:11]([CH3:10])(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 27359194-Amino-3-fluorophenol

Product 1

HCID 64786305N-(2-Fluoro-4-hydroxyphenyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

4-Amino-3-fluorophenol (0.254 g; 2.0 mmol) was dissolved in 10 ml of dry pyridine under nitrogen and cooled to 0° C. Methanesulfonyl chloride (0.17 ml; 2.1 mmol) was added dropwise and stirred for three days at room temperature. The reaction was evaporated, 25 ml of toluene added and evaporated again. Toluene evaporation was repeated. Residue was dissolved in 25 ml of EtOAc, washed with 20 ml of water and evaporated to dryness to give red-brown solid N-(2-fluoro-4-hydroxyphenyl)methanesulfonamide. 1H NMR (400 MHz, DMSO-d6): 2.93 (3H, s), 6.56-6.66 (2H, m), 7.14 (1H, t, J=9.0 Hz), 9.17 (1H, s), 9.98 (1H, s).

Workup

  1. customThe reaction was evaporated
  2. addition25 ml of toluene added
  3. customevaporated again
  4. customToluene evaporation
  5. dissolutionResidue was dissolved in 25 ml of EtOAc
  6. washwashed with 20 ml of water
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-ba401eddf8cd49a1b705a09f6d86b330
Source dataset
uspto-grants-2008_06
Patent number
US07390923B2

Reaction notes

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