1-Bromo-2-fluorobenzene → 2-Chloro-5-((4-fluoro-phenyl)-hydroxy-methyl)-benzenesulfonamide

HRID 1810143Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[F:8].C([Li])(C)(C)C.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]=[O:22])=[CH:17][C:16]=1[S:23]([NH2:26])(=[O:25])=[O:24]>O1CCCC1>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([C:6]2[CH:5]=[CH:4][C:3]([F:8])=[CH:2][CH:7]=2)[OH:22])=[CH:17][C:16]=1[S:23]([NH2:26])(=[O:25])=[O:24]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 590 mg of 1-bromofluorobenzene (1.11 mmol, 3 equivalent) in 10 mL of anhydrous tetrahydrofuran is stirred at −78° C. as 3.9 mL of tert-butyllithium (1.7 M in cyclohexane, 6.66 mmol, 6 equivalent) is added drop-wise. The reaction mixture is stirred at −78° C. for 2 h, then is transfered to a previously prepared a solution of 243 mg of 2 chloro-5-formyl-benzenesulfonamide (1.11 mmol, 1 equivalent) and 0.65 mL of tert-butyllithium (1.7 M in cyclohexane, 1 equivalent) in 10 mL of anhydrous tetrahydrofuran. The reaction is allowed to warm to room temperature and stirred at room temperature for 18 h. The reaction is quenched with 0.1 N HCl and then extracted several times with ethyl acetate. The combined organic extracts are dried over sodium sulfate, and concentrated in vacuo to give 65 mg of the title compound which is carried on without further purification.

Workup

additionis added drop-wise
temperatureto warm to room temperature
stirringstirred at room temperature for 18 h
customThe reaction is quenched with 0.1 N HCl
extractionextracted several times with ethyl acetate
dry with materialThe combined organic extracts are dried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-f4287d1692004b8d8ab3792fc41a1678
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362063B2

Reaction notes

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