Boron tribromide → N-{3-[4-(1,2-diphenyl-but-1-enyl)-phenyl]-acryloyl}-3-hydroxy-benzenesulfonamide

HRID 2253469Notes

Reaction equation

HRID 2253469 reaction equation
[C:1]1([C:7]([C:17]2[CH:22]=[CH:21][C:20]([CH:23]=[CH:24][C:25]([NH:27][S:28]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([O:37]C)[CH:32]=3)(=[O:30])=[O:29])=[O:26])=[CH:19][CH:18]=2)=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:9][CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B(Br)(Br)Br>C(Cl)Cl>[C:1]1([C:7]([C:17]2[CH:22]=[CH:21][C:20]([CH:23]=[CH:24][C:25]([NH:27][S:28]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([OH:37])[CH:32]=3)(=[O:30])=[O:29])=[O:26])=[CH:19][CH:18]=2)=[C:8]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:9][CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 69780580N-{3-[4-(1,2-diphenyl-but-1-enyl)-phenyl]-acryloyl}-3-methoxy-benzenesulfonamide

Product 1

HCID 69780786N-{3-[4-(1,2-diphenyl-but-1-enyl)-phenyl]-acryloyl}-3-hydroxy-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared by treating 1u with boron tribromide (3 eq) in CH2Cl2 at room temperature. Yield (57%); 1H NMR (d6-DMSO) δ 12.15 (br s, 1H), 10.19 (s, 1H), 7.41-7.02 (m, 17H), 6.86 (d, J=8.0 Hz, 2H), 6.42 (d, J=15.7 Hz, 1H), 2.37 (q, J=7.4 Hz, 2H), 0.83 (t, J=7.4 Hz, 3H); APcI m/z: 510 (M+H+)

Workup

  1. customPrepared
  2. customYield (57%)

Sources & evidence

ORD record
ord-059af8fd61a04993a8ff8957cfbc3dcf
Source dataset
uspto-grants-2008_01
Patent number
US07323587B2

Reaction notes

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