Boron tribromide → HCID 51033994, compound

HRID 1623472Notes

Reaction equation

HRID 1623472 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](=[C:15]2/[C:16](=[O:37])[N:17]([CH2:24][C:25]3[CH:30]=[C:29]([O:31]C)[C:28]([O:33]C)=[C:27]([O:35]C)[CH:26]=3)[C:18]3[C:23]/2=[CH:22][CH:21]=[CH:20][CH:19]=3)/[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.ClC1C=CC(/C(=C2\C(=O)N(CC3C=C(OC)C(OC)=C(OC)C=3)C3C\2=CC=CC=3)/C2C=CC=CC=2)=CC=1.B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](=[C:15]2/[C:16](=[O:37])[N:17]([CH2:24][C:25]3[CH:26]=[C:27]([OH:35])[C:28]([OH:33])=[C:29]([OH:31])[CH:30]=3)[C:18]3[C:23]/2=[CH:22][CH:21]=[CH:20][CH:19]=3)/[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 67036557HCID 67036557, compoundHCID 67044041HCID 67044041, compound

Product 1

HCID 51033994HCID 51033994, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[1-(4-chloro-phenyl)-1-phenyl-meth-(E)-ylidene]-1-(3,4,5-trimethoxy-benzyl)-1,3-dihydro-indol-2-one and 3-[1-(4-chloro-phenyl)-1-phenyl-meth-(Z)-ylidene]-1-(3,4,5-trimethoxy-benzyl)-1,3-dihydro-indol-2-one (317 mg, 0.62 mmol) in dichloromethane (5 ml) was added a solution of boron tribromide (1M in CH2Cl2, 3 ml) at room temperature. The mixture was stirred at room temperature for 5 h. After being quenched by pouring into ice water, the mixture was extracted with ethyl acetate, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with (hexane/ethyl acetate=1/1) to give 3-[1-(4-chloro-phenyl)-1-phenyl-meth-(E)-ylidene]-1-(3,4,5-trihydroxy-benzyl)-1,3-dihydro-indol-2-one (60 mg). 1H NMR (300 Hz, CDCl3): δppm 4.66 (s, 2H), 5.60 (b, 1H), 6.31 (s, 2H), 6.56 (d, 1H), 6.67-6.82 (m, 2H), 7.00-7.23 (m, 8H), 7.38 (d, 2H); and 3-[1-(4-Chloro-phenyl)-1-phenyl-meth-(Z)-ylidene]-1-(3,4,5-trihydroxy-benzyl)-1,3-dihydro-indol-2-one (40 mg). 1H NMR (300 Hz, CDCl3): δppm 4.72 (s, 2H), 5.33 (b, 1H), 6.05 (b, 1H), 6.40 (s, 2H), 6.44 (d, 1H), 6.67 (t, 1H), 6.82 (d, 1H), 7.00 (d, 2H), 7.10-7.15 (m, 3H), 7.23-7.26 (m, 2H), 7.37-7.46 (m, 3H).

Workup

  1. customAfter being quenched
  2. additionby pouring into ice water
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash column chromatography on silica gel eluting with (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-c5512c0cafba421daddeb189575aa1b0
Source dataset
uspto-grants-2014_07
Patent number
US08778973B2

Reaction notes

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