Boron tribromide → 7-Hydroxy-2,3,3-trimethyl-2,3-dihydro-isoindol-1-one

HRID 81348Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[C:10](=[O:12])[N:9]([CH3:13])[C:8]2([CH3:15])[CH3:14].B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[C:10](=[O:12])[N:9]([CH3:13])[C:8]2([CH3:15])[CH3:14]

Participants

Conditions

Temperature: -78 °C

Procedure

7-methoxy-2,3,3-trimethyl-2,3-dihydro-isoindol-1-one (0.18 g) is dissolved in CH2Cl2 (4.5 mL) and cooled to −78° C. After the addition of BBr3 (1 molar in CH2Cl2, 2.92 mL) the reaction mixture is allowed to warm up to −10° C. within 3 h. For working up it is diluted with CH2Cl2 and extracted with NaCl solution (H2O, 10%). The organic phase is dried on magnesium sulphate, filtered off from the desiccant and the solvent is eliminated in vacuo. The residue is used in the next reaction step without any further purification.

Workup

temperatureto warm up to −10° C. within 3 h
extractionextracted with NaCl solution (H2O, 10%)
customThe organic phase is dried on magnesium sulphate
filtrationfiltered off from the desiccant and the solvent
customThe residue is used in the next reaction step without any further purification

Sources & evidence

ORD record: ord-b67b5c2832114e57b67e38cafa08118f
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846689B2

Reaction notes

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