Boron tribromide → 4-(2,6-Dichloro-4-nitro-phenoxy)-2-(4-fluoro-benzenesulfonyl)-phenol

HRID 1270587Notes

Reaction equation

HRID 1270587 reaction equation
[Cl:1][C:2]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[C:23]([Cl:30])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([O:21]C)=[C:9]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:10]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[C:23]([Cl:30])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([OH:21])=[C:9]([S:11]([C:14]2[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=2)(=[O:13])=[O:12])[CH:10]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 223449575-(2,6-Dichloro-4-nitro-phenoxy)-2-methoxy-(4-fluoro-benzenesulfonyl)-benzene

Product 1

HCID 223448734-(2,6-Dichloro-4-nitro-phenoxy)-2-(4-fluoro-benzenesulfonyl)-phenolYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(2,6-dichloro-4-nitro-phenoxy)-2-methoxy-(4-fluoro-benzenesulfonyl)-benzene (468 mg, 0.99 mmol) in CH2Cl2 (8 mL) was added boron tribromide (1 M in CH2Cl2, 2.0 mL, 2.0 mmol). The resulting mixture was stirred at room temperature for 2 h and quenched with water (50 mL). After stirring at room temperature for 1 h, the solution was extracted with CH2Cl2 (3×20 mL). The combined organic extracts were dried and concentrated to yield the title compound of Step B (454 mg). The title product of Step B was used in the next step without purification. MS (APCI−) Calc.: 457.0, Found: 456.0 (M−1).

Workup

  1. customquenched with water (50 mL)
  2. stirringAfter stirring at room temperature for 1 h
  3. extractionthe solution was extracted with CH2Cl2 (3×20 mL)
  4. customThe combined organic extracts were dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-baccf4ca2360499f9dcf87da0f6fd84c
Source dataset
uspto-grants-2007_04
Patent number
US07202275B2

Reaction notes

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