Water → 2-Cyclopropylmethanesulfonyl-4-(2,6-dichloro-4-nitro-phenoxy)-phenol

HRID 584029Notes

Reaction equation

HRID 584029 reaction equation
[Cl:1][C:2]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[C:20]([Cl:27])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([O:18]C)=[C:9]([S:11]([CH2:14][CH:15]2[CH2:17][CH2:16]2)(=[O:13])=[O:12])[CH:10]=1.B(Br)(Br)Br.O>C(Cl)Cl>[CH:15]1([CH2:14][S:11]([C:9]2[CH:10]=[C:5]([O:4][C:3]3[C:2]([Cl:1])=[CH:23][C:22]([N+:24]([O-:26])=[O:25])=[CH:21][C:20]=3[Cl:27])[CH:6]=[CH:7][C:8]=2[OH:18])(=[O:12])=[O:13])[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 223448755-(2,6-Dichloro-4-nitro-phenoxy)-2-methoxy-(cyclopropylmethanesulfonyl)-benzene

Product 1

HCID 692587352-Cyclopropylmethanesulfonyl-4-(2,6-dichloro-4-nitro-phenoxy)-phenolYield 49.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(2,6-dichloro-4-nitro-phenoxy)-2-methoxy-(cyclopropyl-methane-sulfonyl)-benzene (160 mg, 0.37 mmol) in CH2Cl2 (3 mL) was added boron tribromide (1M in CH2Cl2, 0.74 mL, 0.74 mmol). The resulting mixture was stirred at room temperature for 2 h and water (15 mL) was added. After stirring at room temperature for 1 h, the solution was extracted with EtOAc (3×20 mL). The combined organic extracts were dried and concentrated. The residue was purified by preparative TLC (100% CH2Cl2) to afford the title compound of Step D (76 mg). MS (APCl−) Calc.: 417.0. Found: 416.2 (M−1).

Workup

  1. stirringAfter stirring at room temperature for 1 h
  2. extractionthe solution was extracted with EtOAc (3×20 mL)
  3. customThe combined organic extracts were dried
  4. concentrationconcentrated
  5. customThe residue was purified by preparative TLC (100% CH2Cl2)

Sources & evidence

ORD record
ord-a1a3049e0b1b4b9a9801d3cb691b504c
Source dataset
uspto-grants-2005_08
Patent number
US06924310B2

Reaction notes

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