Sodium borohydride → 2,9-dibromo-13,13-dimethyl-13H-indeno[1,2-b]anthracene

HRID 1945366Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:22](=[CH:23][CH:24]=1)[C:7]1=[CH:8][C:9]3[CH2:10][C:11]4[CH:12]=[CH:13][C:14]([Br:21])=[CH:15][C:16]=4[C:17](=O)[C:18]=3[CH:19]=[C:6]1[C:5]2([CH3:26])[CH3:25].[BH4-].[Na+]>CC(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:22](=[CH:23][CH:24]=1)[C:7]1=[CH:8][C:9]3[CH:10]=[C:11]4[C:16](=[CH:17][C:18]=3[CH:19]=[C:6]1[C:5]2([CH3:26])[CH3:25])[CH:15]=[C:14]([Br:21])[CH:13]=[CH:12]4

Participants

Conditions

Temperature: 100 °C

Procedure

2,9-Dibromo-13,13-dimethyl-6H-indeno[1,2-b]anthracen-11(13H)-one (13 g, 1 eq, 0.027 mol) was placed in a flask, and IPA (200 ml) was added thereto. Then, sodium borohydride (3.1 g, 3 eq, 0.081 mol) was gradually added at 0° C., the reaction mixture was stirred at 100° C. while heating for 24-36 hours and cooled to room temperature, and ice water was gradually added thereto. The resultant solid was filtered, several times washed with distilled water, dried and purified by column chromatography to give 2,9-dibromo-13,13-dimethyl-13H-indeno[1,2-b]anthracene (EMI 11) (8.5 g, yield=70%).

Workup

temperaturewhile heating for 24-36 hours
temperaturecooled to room temperature
filtrationThe resultant solid was filtered
washseveral times washed with distilled water
customdried
custompurified by column chromatography

Sources & evidence

ORD record: ord-c5e7c1ecdfc94df28278183cd76da6b6
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08395144B2

Reaction notes

Loading…