Water → HCID 136406071, compound

HRID 1011488Notes

Reaction equation

HRID 1011488 reaction equation
C[O:2][C:3]1[CH:23]=[CH:22][C:6]2[C:7]([CH:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=3)[C:11]#[N:12])=[N:8][O:9][C:5]=2[CH:4]=1.B(Br)(Br)Br.O>C(Cl)Cl>[OH:2][C:3]1[CH:23]=[CH:22][C:6]2[C:7]([CH:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)[C:11]#[N:12])=[N:8][O:9][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 23117155HCID 23117155, compound

Product 1

HCID 136406071HCID 136406071, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(6-methoxy-1,2-benzisoxazol-3-yl)-3-(4-methoxyphenyl)propanenitrile (1.5 g, 4.9 mmoles) in CH2Cl2 (100 ml) under N2, was added BBr3 1M in CH2Cl2 (4 eq, 20 ml). The mixture was refluxed for 2 h, poured into water and extracted with EtOAc, dried over Na2SO4, filtered and concentrated under vacuum to give the crude product. Purification by flash chromatography (CH2Cl2/MeOH 98/2) and crystallisation from EtOH yielded the expected crystals (850 mg, 62%). mp 214° C.

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. extractionextracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customto give the crude product
  7. customPurification
  8. customby flash chromatography (CH2Cl2/MeOH 98/2) and crystallisation from EtOH

Sources & evidence

ORD record
ord-c3f43c5a88eb47708efb057f1fe321dd
Source dataset
uspto-grants-2011_07
Patent number
US07977364B2

Reaction notes

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