Boron tribromide → 8-Hydroxy-1,3,4,5-tetrahydrobenzo[b]azepin-2-one

HRID 490696Notes

Reaction equation

HRID 490696 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH2:11][CH2:10][C:9](=[O:13])[NH:8][C:7]=2[CH:14]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH2:11][CH2:10][C:9](=[O:13])[NH:8][C:7]=2[CH:14]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 6769538-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one

Product 1

HCID 99205198-Hydroxy-1,3,4,5-tetrahydrobenzo[b]azepin-2-oneYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 8-methoxy-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (116 mg, 0.607 mmol) in CH2Cl2 (20 mL) at 0° C. is treated with BBr3 (1.2 mL, 1.0 M in CH2Cl2) added dropwise. The mixture is stirred for 16 hours at room temperature and then quenched with water dropwise. The suspension is filtered and the solid is rinsed with MeOH (1.0 mL) and dried under vacuum to obtain pure product (95 mg, 89%).

Workup

  1. additionadded dropwise
  2. customquenched with water dropwise
  3. filtrationThe suspension is filtered
  4. washthe solid is rinsed with MeOH (1.0 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-1f73fba40ba5460aafd874fbeba60480
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Reaction notes

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