Dichloromethane → 4-(3-Bromophenyl)-4-methyl[1,2,3]-oxathiazolidine-2,2-dioxide

HRID 2358007Notes

Reaction equation

HRID 2358007 reaction equation
C(OC([N:8]1[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Br:20])[CH:15]=2)([CH3:13])[CH2:11][O:10][S:9]1(=[O:22])=[O:21])=O)(C)(C)C.C(Cl)Cl>C(O)(C(F)(F)F)=O>[Br:20][C:16]1[CH:15]=[C:14]([C:12]2([CH3:13])[CH2:11][O:10][S:9](=[O:22])(=[O:21])[NH:8]2)[CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 866051283-(Tert-butoxycarbonyl)-4-(3-bromophenyl)-4-methyl-[1,2,3]-oxathiazolidine-2,2-dioxide

Product 1

HCID 866051294-(3-Bromophenyl)-4-methyl[1,2,3]-oxathiazolidine-2,2-dioxideYield 91%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

3-(tert-Butoxycarbonyl)-4-(3-bromophenyl)-4-methyl-[1,2,3]-oxathiazolidine-2,2-dioxide (DC4; R6=Me) (10.8 g, 28 mmol) was dissolved in 25% TFA in DCM (40 mL, 5 eq) and the mixture was left standing at RT for 3 h. The mixture was concentrated in vacuo to give 7.3 g (91%) of 4-(3-bromophenyl)-4-methyl-[1,2,3]-oxathiazolidine-2,2-dioxide as a yellow oil. 1H NMR (CDCl3) δ 7.59 (t, J=1.8 Hz, 1H), 7.48-7.52 (m, 1H), 7.39-7.42 (m, 1H), 7.30 (t, J=8.1 Hz, 1H), 4.59 (m, 2H), 1.82 (s, 3H).

Workup

  1. waitthe mixture was left
  2. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-b3983ab40bd542c99147ce718e75cc56
Source dataset
uspto-grants-2010_07
Patent number
US07763609B2

Reaction notes

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