1,2-Dibromoethane → HCID 10093123, compound

HRID 260300Notes

Reaction equation

[CH2:1]([C:3]1[C@@H:4]2[C@@H:20]([C@:21]3([CH3:29])[C:26]([CH:27]=1)=[CH:25][C:24](=[O:28])[CH2:23][CH2:22]3)[CH2:19][CH2:18][C@@:17]1([CH3:30])[C@H:5]2[CH2:6][CH2:7][C@@H:8]1[C@H:9]([CH3:16])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[CH3:2].[Li].BrCCBr.[Cl-].[NH4+]>N.C1COCC1.C1(C)C=CC=CC=1>[CH2:1]([C@H:3]1[CH:27]=[C:26]2[C@:21]([CH3:29])([CH2:22][CH2:23][C:24](=[O:28])[CH2:25]2)[C@@H:20]2[C@@H:4]1[C@H:5]1[C@:17]([CH3:30])([CH2:18][CH2:19]2)[C@@H:8]([C@H:9]([CH3:16])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:7][CH2:6]1)[CH3:2]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 3.1 g of 3, from Example 3, in 46 ml ammonia, 10 ml THF, 10 milliliters toluene, was added 449 mg of metallic lithium in small pieces. After stirring the blue solution for 2 hours at -78° C., a solution of 1,2-dibromoethane in 2 ml THF was added. After stirring the solution at -78° C. for 10 minutes, 2.1 g of ammonium chloride was added and the mixture stirred for 10 minutes. The excess ammonia was removed by evaporation under a nitrogen stream. The reaction mixture was diluted with brine, extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated to yield crude brown viscous liquid 4 which was used as such in Example 5. Rf=0.70 (20% EtOAc/hexane). Mass Spec. 412 (EI); calculated MW 412.70.

Workup

stirringAfter stirring the solution at -78° C. for 10 minutes
stirringthe mixture stirred for 10 minutes
customThe excess ammonia was removed by evaporation under a nitrogen stream
additionThe reaction mixture was diluted with brine
extractionextracted with ethyl acetate
washThe organic layer was washed with brine
customdried
concentrationconcentrated

Sources & evidence

ORD record: ord-34a285c47c854ebb995bce39da5f96fa
Source dataset: uspto-grants-1996_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05527807

Reaction notes

Loading…