2-Bromoethanol → HCID 57886373, compound

HRID 1818774Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[NH:10][S:9]2(=[O:18])=[O:17])=[C:4]([CH3:19])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:39][CH2:40][CH2:41]O.CC(OC(/N=N/C(OC(C)C)=O)=O)C>>[Br:39][CH2:40][CH2:41][N:10]1[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=2[CH3:19])[S:9]1(=[O:17])=[O:18]

Participants

Reactant 4

HCID 108982-Bromoethanol

HCID 11776Triphenylphosphine

HCID 5363146Diisopropyl azodicarboxylate

HCID 57886335HCID 57886335, compound

Product 1

HCID 57886373HCID 57886373, compound

Procedure

1-(4-fluoro-2-methylphenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (prepared analogously as described in general procedure I, 0.35 g, 1.3 mmol) was treated with triphenylphosphine (0.46 g, 1.5 mmol), 2-bromoethanol (0.21 g, 1.4 mmol) and diisopropylazodicarboxylate (0.35 g, 1.7 mmol) to provide 0.32 g of 1-(2-bromoethyl)-3-(4-fluoro-2-methylphenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide. HRMS: calculated for C15H14BrFN2O2S, 383.99434; found (EI, M+), 383.9958

Sources & evidence

ORD record: ord-91d060d7c8fe4ea885c2c002c3ddd375
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601722B2

Reaction notes

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