Hexane → 2-(4-Hydroxy-3,5-dimethylphenyl)-4-(2,4,6-trifluorobenzyl)-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxide

HRID 1772955Notes

Reaction equation

HRID 1772955 reaction equation
C[O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([N:10]2[C:15](=[O:16])[N:14]([CH2:17][C:18]3[C:23]([F:24])=[CH:22][C:21]([F:25])=[CH:20][C:19]=3[F:26])[C:13]3[CH:27]=[CH:28][CH:29]=[CH:30][C:12]=3[S:11]2(=[O:32])=[O:31])=[CH:5][C:4]=1[CH3:33].B(Br)(Br)Br.CCCCCC.C([O-])(O)=O.[Na+]>C(Cl)Cl.CCOC(C)=O>[OH:2][C:3]1[C:4]([CH3:33])=[CH:5][C:6]([N:10]2[C:15](=[O:16])[N:14]([CH2:17][C:18]3[C:19]([F:26])=[CH:20][C:21]([F:25])=[CH:22][C:23]=3[F:24])[C:13]3[CH:27]=[CH:28][CH:29]=[CH:30][C:12]=3[S:11]2(=[O:32])=[O:31])=[CH:7][C:8]=1[CH3:9]

Participants

7

Reactant 4

HCID 8058HexaneHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 727220852-(4-methoxy-3,5-dimethylphenyl)-4-(2,4,6-trifluorobenzyl)-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxide

Product 1

HCID 727218952-(4-Hydroxy-3,5-dimethylphenyl)-4-(2,4,6-trifluorobenzyl)-2H-1,2,4-benzothiadiazin-3(4H)-one 1,1-dioxideYield 57.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (115) (0.2 g, 0.42 mmol) in DCM (5 mL) was added boron tribromide (1.0M solution in DCM, 0.46 mL, 0.46 mmol) at −70° C. The resulting mixture was stirred for approximately two h at rt with TLC monitoring (hexane:EtOAc, 1:1). The reaction mixture was poured into saturated aqueous NaHCO3 solution (50 mL), extracted with EtOAc (3×50 mL), and the combined organic layer was dried over Na2SO4 and concentrated in vacuo. Purification by trituration with DCM in pentane (1:9) yielded the title compound (0.11 g, 0.24 mmol).

Workup

  1. extractionextracted with EtOAc (3×50 mL)
  2. dry with materialthe combined organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customPurification by trituration with DCM in pentane (1:9)

Sources & evidence

ORD record
ord-fb35541145b54fb29c7f3ea4cca1ba92
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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