1-Propanol → 2-Bromo-4-ethylsulfonyl-1-propoxybenzene

HRID 575695Notes

Reaction equation

[CH2:1]([OH:4])[CH2:2][CH3:3].[H-].[Na+].[Br:7][C:8]1[CH:13]=[C:12]([S:14]([CH2:17][CH3:18])(=[O:16])=[O:15])[CH:11]=[CH:10][C:9]=1F.[NH4+].[Cl-]>C1COCC1.CC(=O)OCC>[Br:7][C:8]1[CH:13]=[C:12]([S:14]([CH2:17][CH3:18])(=[O:16])=[O:15])[CH:11]=[CH:10][C:9]=1[O:4][CH2:1][CH2:2][CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of n-propanol (224 mg, 3.74 mmol) in THF (10 mL) was added NaH (112 mg, 2.80 mmol, 60% in mineral oil) at 0° C. After stirring at 0° C. for 30 min, 2-bromo-4-(ethanesulfonyl)-1-fluorobenzene (500 mg, 1.87 mmol) was added and the mixture was stirred at room temperature for 4 h. Addition of saturated NH4Cl (10 mL) followed by EA extractive work up gave the title compound (300 mg, yield: 52.3%) which was carried on directly.

Workup

stirringthe mixture was stirred at room temperature for 4 h

Sources & evidence

ORD record: ord-28661011b23e480f9d4f089803101aa5
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034900B2

Reaction notes

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