1,4-Dibromobenzene → 4-(4-Bromophenyl)-1lambda~6~,4-thiazinane-1,1-dione

HRID 1023307Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.[NH:9]1[CH2:14][CH2:13][S:12](=[O:16])(=[O:15])[CH2:11][CH2:10]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])(C)C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([N:9]2[CH2:14][CH2:13][S:12](=[O:16])(=[O:15])[CH2:11][CH2:10]2)=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1,4-dibromobenzene (118 mg, 0.5 mmol), thiomorpholine-1,1-dioxide (68 mg, 0.5 mmol), Pd2 dba3 (12 mg, 2.5 mol %), BINAP (24 mg, 7.5 mol %), sodium 2-methylpropan-2-olate (72 mg, 0.75 mmol) and toluene (2 mL) was stirred at 80° C. for overnight. The reaction mixture was cooled down to room temperature and worked-up. The residue was purified on slilica gel flash column chromatography (eluent: 0-50% EtOAc in hexane) to afford 4-(4-bromophenyl)thiomorpholine-1,1-dioxide as a white solid.

Workup

temperatureThe reaction mixture was cooled down to room temperature
customThe residue was purified on slilica gel flash column chromatography (eluent: 0-50% EtOAc in hexane)

Sources & evidence

ORD record: ord-2c52fa3306c447fc92ae716e9465720e
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722692B2

Reaction notes

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