Triphenylphosphine → 5-bromo-2,3-dihydro-1H-isoindol-1-one

HRID 1663180Notes

Reaction equation

HRID 1663180 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[C:4]([CH2:11]O)[CH:3]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:9][CH:10]=1)[C:6](=[O:7])[NH:8][CH2:11]2

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 57926938HCID 57926938, compound

Product 1

HCID 226071195-bromo-2,3-dihydro-1H-isoindol-1-oneYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromo-2-(hydroxymethyl)benzamide III-2 (3.50 g, 15.2 mmol) in THF (100 mL) was added Ph3P (4.78 g, 18.3 mmol) and DIAD (3.38 g, 16.7 mmol). The reaction was stirred at room temperature 20 h. The reaction mixture was concentrated under vacuum and purified by column chromatography (silica gel) using 0 to 25% EtOAc in hexanes to afford 5-bromoisoindolin-1-one III-3 as a white solid (786 mg, 24%) as a white solid; 1H-nmr (400 MHz, CDCl3) δ 7.80 (d, J=8.0 Hz, 1H), 7.70 (s, 1H), 7.67 (s, 2H), 5.31 (s, 2H); LC (254 nM) 4.88 min (>98%); MS (ESI) m/z=212.8, 214.8.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. custompurified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-c07f2190a1ee42e4b887b6dab07e93e6
Source dataset
uspto-grants-2011_10
Patent number
US08034806B2

Reaction notes

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