Boron tribromide → HCID 58342005, compound

HRID 339537Notes

Reaction equation

HRID 339537 reaction equation
[N+:1]([C:4]1[CH:29]=[CH:28][C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[S:18][C:19]4[CH:25]=[C:24]([O:26]C)[CH:23]=[CH:22][C:20]=4[N:21]=3)=[CH:13][CH:12]=2)=[O:9])=[CH:6][C:5]=1[C:30]([F:33])([F:32])[F:31])([O-:3])=[O:2].B(Br)(Br)Br.CCOC(C)=O.CCCCCC>C(Cl)Cl>[N+:1]([C:4]1[CH:29]=[CH:28][C:7]([C:8]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[S:18][C:19]4[CH:25]=[C:24]([OH:26])[CH:23]=[CH:22][C:20]=4[N:21]=3)=[CH:15][CH:16]=2)=[O:9])=[CH:6][C:5]=1[C:30]([F:33])([F:32])[F:31])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 21226206Ethyl acetate hexaneHCID 67311687HCID 67311687, compound

Product 1

HCID 58342005HCID 58342005, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared as described in the Demethylation section using 4-nitro-3-trifluoromethyl-N-[4-(6-methoxybenzothiazol-2-yl)-phenyl]-benzamide (0.10 g, 0.21 mmol) in dry DCM (10 ml) and BBr3 (1.0 M solution in DCM, 1.1 ml, 1.1 mmol) to give the title compound (0.07 g, 71%) as a yellow solid after work-up and flash chromatography (3:1 EtOAc/Hexane).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-7421ba51911846819b5a1fc945beaf96
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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