Acetic Acid → Methyl 2-[5-bromo-2-(4-methanesulfonylphenyl)thiophen-3-yl]acetate

HRID 2199575Notes

Reaction equation

C1C(=O)N([Br:8])C(=O)C1.[CH3:9][S:10]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[S:20][CH:21]=[CH:22][C:23]=2[CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:15][CH:14]=1)(=[O:12])=[O:11].CC(O)=O>CO.C(Cl)(Cl)Cl>[Br:8][C:21]1[S:20][C:19]([C:16]2[CH:15]=[CH:14][C:13]([S:10]([CH3:9])(=[O:12])=[O:11])=[CH:18][CH:17]=2)=[C:23]([CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH:22]=1

Participants

Conditions

Temperature: 0 °C

Procedure

NBS (209 mg, 1.18 mmol) was added in small portions to a stirred solution of Intermediate Y (365 mg, 1.18 mmol) in a mixture of MeOH (10 ml) and chloroform (5 ml) at 0° C. AcOH (0.250 ml) was added and the reaction was stirred at 0° C. for 1 hour then at r.t. for 3 hours. More NBS (35 mg, 0.20 mmol) was added at 0° C. and the reaction was stirred at r.t. over night. A new reaction was also started. NBS (342 mg, 1.92 mmol) was added in small portions to a stirred solution of Intermediate Y (519 mg, 1.67 mmol) in a mixture of MeOH (15 ml) and chloroform (7 ml) at 0° C. AcOH (0.50 ml) was added and the reaction was stirred at r.t. over night.

Workup

waitat r.t. for 3 hours
stirringthe reaction was stirred at r.t. over night
customA new reaction
stirringthe reaction was stirred at r.t. over night

Sources & evidence

ORD record: ord-a153574c1492456483680e7e878b5fcc
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359311B2

Reaction notes

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