Hydrogen Bromide → 4-(2-Bromo-6-methylpyridine-3-sulfonyl)-phenol

HRID 1796323Notes

Reaction equation

HRID 1796323 reaction equation
Cl[C:2]1[C:7]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:6][CH:5]=[C:4]([CH3:19])[N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[BrH:26]>O>[Br:26][C:2]1[C:7]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:6][CH:5]=[C:4]([CH3:19])[N:3]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 10340Sodium CarbonateHCID 221816772-Chloro-3-(4-methoxybenzenesulfonyl)-6-methylpyridine

Product 1

HCID 221816884-(2-Bromo-6-methylpyridine-3-sulfonyl)-phenolYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

2-Chloro-3-(4-methoxybenzenesulfonyl)-6-methylpyridine (4.74 g, 15.92 mmol) was suspended in HBr (84 mL, 48%). The orange reaction mixture was heated at 110° C. for 24 h. The reaction mixture was cooled to rt, diluted with H2O, and was treated with Na2CO3 until neutral. The aqueous layer was extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated to afford a colorless solid (3.22 g, 62% yield) which was used without further purification: mp 99–102° C.; 1H NMR (300 MHz, CDCl3) δ 8.52 (d, J=7.7 Hz, 1H), 7.86 (d, J=8.8 Hz, 2H), 7.35 (d, J=8.0 Hz, 1H), 6.95 (d, J=9.1 Hz, 2H), 2.63 (s, 3H); LRMS (APCI) m/z 328.0 [(M+H)+, calcd for C12H11NO3BrS, 328.0].

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. extractionThe aqueous layer was extracted with EtOAc (3×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d37a819d42bf40faa19658ece5cb65e2
Source dataset
uspto-grants-2006_04
Patent number
US07030145B2

Reaction notes

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