Benzyl Bromide → 5-(Dibenzylamino)-2-benzofuran-1(3H)-one

HRID 1829035Notes

Reaction equation

[NH2:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[CH:3]=1.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH:20](N(C(C)C)CC)([CH3:22])[CH3:21].[CH2:29]1[CH2:33]O[CH2:31][CH2:30]1>>[CH2:12]([N:1]([CH2:31][C:30]1[CH:22]=[CH:20][CH:21]=[CH:33][CH:29]=1)[C:2]1[CH:3]=[C:4]2[C:5](=[CH:10][CH:11]=1)[C:6](=[O:9])[O:7][CH2:8]2)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Reactant 4

HCID 7498Benzyl Bromide

HCID 8028Tetrahydrofuran

HCID 81531Diisopropylethylamine

HCID 7206695-Aminophthalide

Product 1

HCID 220614885-(Dibenzylamino)-2-benzofuran-1(3H)-oneYield 31%

Conditions

Temperature: 50 °C

Procedure

A mixture of 5-amino-2-benzofuran-1(3H)-one (100 mg, 0.67 mmol), benzyl bromide (319 μl, 2.68 mmol), and diisopropylethylamine (350 μl, 2.01 mmol) in THF (2.0 ml) was heated at 50° C. for 65 hours. The reaction was partitioned between water and EtOAc. The organic layer was washed with water, brine, dried with Na2SO4 and rotary evaporated. The yellow oil was triturated at room temperature with 10% EtOAc/hexane and then chromatographed (20% to 40% EtOAc/hexane gradient) to give 5-dibenzylamino-3H-isobenzofuran-1-one as a white solid (136 mg, 31%).

Workup

customThe reaction was partitioned between water and EtOAc
washThe organic layer was washed with water, brine
dry with materialdried with Na2SO4 and rotary evaporated
customThe yellow oil was triturated at room temperature with 10% EtOAc/hexane
customchromatographed (20% to 40% EtOAc/hexane gradient)

Sources & evidence

ORD record: ord-e52d2174dfd34d4b80a014c407536b9c
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07060844B2

Reaction notes

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