Boron tribromide → HCID 57777278, compound

HRID 660711Notes

Reaction equation

C([O:8][C:9]1[CH:14]=[C:13]([CH:15]=[CH2:16])[CH:12]=[CH:11][C:10]=1[N:17]1[S:21](=[O:23])(=[O:22])[NH:20][C:19](=[O:24])[CH2:18]1)C1C=CC=CC=1.B(Br)(Br)Br>C(Cl)Cl>[OH:8][C:9]1[CH:14]=[C:13]([CH:15]=[CH2:16])[CH:12]=[CH:11][C:10]=1[N:17]1[S:21](=[O:23])(=[O:22])[NH:20][C:19](=[O:24])[CH2:18]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5-(2-benzyloxy-4-vinylphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (73 mg, 0.21 mmol) in CH2Cl2 (4 mL) at 0° C. is added dropwise 1M BBr3 (0.32 mL, 0.32 mmol) in CH2Cl2 and the reaction is stirred at 0° C. for 30 min. The mixture is quenched with water (1 mL) followed by washing with Et2O. The aqueous layer is concentrated under reduced pressure and the crude residue is purified by chromatography on a C18 column using a gradient of 0-15% EtOH/water as eluent to give the title compound: (M−H)−=253; 1H NMR (MeOD) δ 7.32 (d, J=8.0 Hz, 1H), 6.87 (d, J=2.0 Hz, 1H), 6.79 (dd, J=8, 2 Hz, 1H), 4.69 (q, J=6.48 Hz, 1H), 4.26 (s, 2H), 2.63 (s, 1H), 1.34 (d, J=6.57 Hz, 3H).

Workup

customThe mixture is quenched with water (1 mL)
washby washing with Et2O
concentrationThe aqueous layer is concentrated under reduced pressure
customthe crude residue is purified by chromatography on a C18 column

Sources & evidence

ORD record: ord-5f37bc812ca64a8fbd9fac02cf99ce23
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084448B2

Reaction notes

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