2-Amino-4-(methylsulfonyl)phenol → HCID 4594979, compound

HRID 255265Notes

Reaction equation

HRID 255265 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([NH2:12])[CH:6]=1)(=[O:4])=[O:3].C(=O)(O)[O-].[Na+].Br[CH2:19][C:20](Br)=[O:21]>C(Cl)(Cl)Cl>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]2[O:11][CH2:19][C:20](=[O:21])[NH:12][C:7]=2[CH:6]=1)(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 73822-Amino-4-(methylsulfonyl)phenol2×HCID 61147Bromoacetyl bromideHCID 516892Sodium Bicarbonate

Product 1

HCID 4594979HCID 4594979, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

4-Methylsulfonyl-2-aminophenol (Intermediate 102) (690 mg, 3.68 mmol) was dissolved in chloroform (30 mL) and saturated sodium bicarbonate (20 mL). The biphasic reaction mixture was cooled to 0° C. and bromoacetyl bromide (889 mg, 4.42 mmol) was added dropwise. The reaction was stirred overnight at room temperature. The layers were separated and the aqueous layer was filtered to yield the desired product as a solid, 280 mg (33%).

Workup

  1. customThe biphasic reaction mixture
  2. customThe layers were separated
  3. filtrationthe aqueous layer was filtered

Sources & evidence

ORD record
ord-29e785d26707406d9a026b84f1aecf08
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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