Water → HCID 135982275, compound

HRID 2042601Notes

Reaction equation

HRID 2042601 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:10][CH2:11][C:12](=[O:21])[N:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[N:14]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br.[NH4+].[Cl-].O>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:10][CH2:11][C:12](=[O:21])[N:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[N:14]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25134Boron tribromideHCID 25517Ammonium ChlorideHCID 59651929HCID 59651929, compound

Product 1

HCID 135982275HCID 135982275, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from step 1 (1.25 g, 4.4 mmol) in DCM (30 mL) was added BBr3 (30 mL, 1 M in DCM) dropwise at 0° C. After stirring 4 h at rt, the mixture was cooled to 0-5° C. on an ice-bath while saturated NH4Cl solution (30 mL) was added dropwise. Additional water was added and the DCM was removed at reduced pressure. The solid was collected and dried to give 1.1 g (93%) of a tan solid; Mp>220° C.; MS m/z 268 (M+H).

Workup

  1. additionwas added dropwise
  2. customthe DCM was removed at reduced pressure
  3. customThe solid was collected
  4. customdried

Sources & evidence

ORD record
ord-508671950c584647a01d99474a93ef8b
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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