Ethyl acetate hexane → HCID 136400552, compound

HRID 339584Notes

Reaction equation

HRID 339584 reaction equation
C[O:2][C:3]1[CH:31]=[CH:30][C:6]2[N:7]=[C:8]([C:10]3[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]4[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][C:19]=4[C:26]([F:29])([F:28])[F:27])=[CH:12][CH:11]=3)[S:9][C:5]=2[CH:4]=1.CCCCCC.CCOC(C)=O>C(Cl)Cl.B(Br)(Br)Br>[OH:24][C:21]1[CH:22]=[CH:23][C:18](/[CH:17]=[CH:16]/[C:13]2[CH:12]=[CH:11][C:10]([C:8]3[S:9][C:5]4[CH:4]=[C:3]([OH:2])[CH:31]=[CH:30][C:6]=4[N:7]=3)=[CH:15][CH:14]=2)=[C:19]([C:26]([F:29])([F:28])[F:27])[CH:20]=1

Participants

5

Reactant 2

HCID 21226206Ethyl acetate hexaneHCID 67237852HCID 67237852, compound

Product 1

HCID 136400552HCID 136400552, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 25134Boron tribromideSolvent

Procedure

Prepared as described in the Demethylation section above using 6-methoxy-2-(4-{(E)-2-[4-methoxy-2-(trifluoromethyl)phenyl]ethenyl}phenyl)-1,3-benzothiazole (0.30 g, 0.68 mmol) in dry DCM (10 ml) and BBr3 in DCM (1.0 M, 1.40 ml, 1.40 mmol) at −78° C. give the title compound (0.229 g, 81%) as a yellow solid after work-up and flash chromatography (1:1 Hexane/EtOAc).

Workup

  1. customPrepared
  2. customat −78° C.

Sources & evidence

ORD record
ord-42c1b93c15a54741beb3b53c20967ccf
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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