Methanol → 4-Fluoro-2-(morpholine-4-sulfonyl)-phenol

HRID 1971835

Reaction equation

HRID 1971835 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:17]C)=[C:6]([S:8]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)(=[O:10])=[O:9])[CH:7]=1.BrB(Br)Br.CO>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:17])=[C:6]([S:8]([N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)(=[O:9])=[O:10])[CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 8499944-(5-Fluoro-2-methoxy-benzenesulfonyl)-morpholine

Product 1

HCID 581269904-Fluoro-2-(morpholine-4-sulfonyl)-phenolYield 90.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(5-fluoro-2-methoxyphenylsulfonyl)morpholine (0.5 g 1.8 mmol) in CH2Cl2 (10 ml) was added dropwise a solution of tribromoborane (0.593 mg 2.36 mmol) in CH2Cl2 (20 ml) at 0° C. The mixture was stirred at room temperature for 1 h, after which methanol (10 ml) was added to quench the reaction. The solvent was evaporated under reduced pressure and ethyl acetate (30 ml) was added, washed with water and then brine, dried and concentrated into dryness to give the product (427 mg, 90% yield).

Workup

  1. customto quench
  2. customthe reaction
  3. customThe solvent was evaporated under reduced pressure and ethyl acetate (30 ml)
  4. additionwas added
  5. washwashed with water
  6. dry with materialbrine, dried
  7. concentrationconcentrated into dryness

Sources & evidence

ORD record
ord-ff47d3c2911042d6b8247f41505c199f
Source dataset
uspto-grants-2013_04
Patent number
US08431581B2

Linked notes

Loading…