Water → Methyl 5-bromo4-oxo-4,5,6,7-tetrahydro-1-benzothiophene-5-carboxylate

HRID 1070609Notes

Reaction equation

[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][S:10][C:6]=2[CH2:5][CH2:4][CH:3]1[C:11]([O:13][CH3:14])=[O:12].[Br:15]Br.O>CCOCC.C(Cl)(Cl)(Cl)Cl>[Br:15][C:3]1([C:11]([O:13][CH3:14])=[O:12])[C:2](=[O:1])[C:7]2[CH:8]=[CH:9][S:10][C:6]=2[CH2:5][CH2:4]1

Participants

Conditions

Temperature: -10 °C

Procedure

Methyl 4-oxo-4,5,6,7-tetrahydro-1-benzothiophene-5-carboxylate (Preparation 11, 3.50 g) is dissolved in anhydrous ether (30 mL) and carbon tetrachloride (20 mL). This solution is cooled to −10° C. and a solution of bromine (2.66 g) in carbon tetrachloride (5 mL) with 3 drops of ether. Each drop of the bromine solution is added only after the orange color dissipated from the prior drop. After completion of addition, the solution is allowed to stir for 15 minutes at −10° C., 15 minutes at 0° C., and then overnight at rt. This reaction mixture is poured into water (100 mL) and extracted with ether (100 mL). The ether phase is washed with brine, dried over Na2SO4, filtered, and concentrated to give 4.80 g (99%) of the title compound as a yellow oil. Physical characteristics: MS (ESI+) m/z 289.0/291.0 (M+H)+.

Workup

additionAfter completion of addition
customovernight
customat rt
extractionextracted with ether (100 mL)
washThe ether phase is washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-d7f8614198744388bd26b4d14a84ace0
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06903097B2

Reaction notes

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