Water → 5-Hydroxy-3,3-dimethylisoindolin-1-one

HRID 1737309Notes

Reaction equation

HRID 1737309 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[NH:11][C:10]2([CH3:18])[CH3:17].O>C(Cl)Cl>[OH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[NH:11][C:10]2([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromide2×HCID 105838765-Methoxy-3,3-dimethylisoindolin-1-one

Product 1

HCID 107736505-Hydroxy-3,3-dimethylisoindolin-1-oneYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A 1 M solution of BBr3 in CH2Cl2 (88.0 mL, 88.0 mmol) is dissolved in dry CH2Cl2 under N2. A solution of lactam 57 (7.65 g, 40.0 mmol) in CH2Cl2 (50 mL) is added to the BBr3 solution dropwise over 10 min. The resulting mixture is stirred at rt overnight. The reaction mixture is poured into water and extracted with EtOAc (3×). The organic phase is dried (MgSO4), filtered, and evaporated, leaving the product 62 as a white solid (4.03 g, 57%), mp 231-233° C., which requires no purification. 1H NMR (DMSO-d6, 2.50 ppm) 8.18 (s, 1), 7.28 (d, 1, J=8.5), 6.75 (d, 1, J=1.6), 6.67 (dd, 1, J=8.5, 1.6), 1.25 (s, 6); 13C NMR (CDCl3 +DMSO-d6) 169.30, 161.06, 155.40, 124.68, 121.53, 115.39, 107.26, 57.98, 27.47; MS (MW=177.2, EI, eE=70 eV) m/z 177 (M+), 163, 162 (base peak).

Workup

  1. extractionextracted with EtOAc (3×)
  2. dry with materialThe organic phase is dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-39a30563791d41c6910336e63557c569
Source dataset
uspto-grants-1999_10
Patent number
US05962469

Reaction notes

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