Sodium Hydroxide → 5-(2,6-Dichloro-4-nitro-phenoxy)-2-methoxy-(cyclopropylmethanesulfonyl)-benzene

HRID 1270596Notes

Reaction equation

[Cl:1][C:2]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[C:16]([Cl:23])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([O:14][CH3:15])=[C:9]([S:11]([OH:13])=[O:12])[CH:10]=1.[OH-].[Na+].[CH:26]1([CH2:29]Br)[CH2:28][CH2:27]1>C(O)C>[Cl:1][C:2]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[C:16]([Cl:23])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([O:14][CH3:15])=[C:9]([S:11]([CH2:29][CH:26]2[CH2:28][CH2:27]2)(=[O:13])=[O:12])[CH:10]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 5-(2,6-dichloro-4-nitro-phenoxy)-2-methoxy-benzenesulfinic acid (1.0 g, 2.64 mmol) in ethanol was added NaOH (116 mg, 2.89 mmol) and cyclopropylmethyl bromide (1.40 mL, 14.5 mmol). The resulting mixture was stirred at 70° C. for 6 h, then at 50° C. for 20 h and concentrated to dryness. The residue was dissolved in 1 N HCl (40 mL) and extracted with EtOAc (4×40 mL). The combined organic extracts were dried and concentrated. The residue was purified by preparative TLC (CH2Cl2: Hex=4:1) to give the title compound of Step C (160 mg) as a solid. MS (APCI−) Calc.: 431.0, Found: 430.2 (M−1).

Workup

waitat 50° C. for 20 h
concentrationconcentrated to dryness
dissolutionThe residue was dissolved in 1 N HCl (40 mL)
extractionextracted with EtOAc (4×40 mL)
customThe combined organic extracts were dried
concentrationconcentrated
customThe residue was purified by preparative TLC (CH2Cl2: Hex=4:1)

Sources & evidence

ORD record: ord-c7e63ce98f184ea591edb0d28b3770cd
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07202275B2

Reaction notes

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