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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1768Generated: October 26, 2026

Boron tribromide → cis-(+/-)-5-Bromo-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-6-ol

https://huagongshe.com/reaction/1768

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBoron tribromideHCID 25134—
Reactantcis-(+/-)-5-Bromo-1,2,3,3a,8,8a-hexahydro-6-methoxy-1,3a,8-trimethylpyrrolo[2,3-b]indolHCID 67752673—
SolventDichloromethaneHCID 6344—
Productcis-(+/-)-5-Bromo-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-6-olHCID 67753116—

Reaction Steps

cis-(±)-5-Bromo-1,2,3,3a,8,8a-hexahydro-6-methoxy- 1,3a,8-trimethyl-pyrrolo[2,3-b]indole (11 g) was dissolved in dry DCM (200 ml) and added dropwise at 0° C. to a stirred solution of BBr3 in DCM (300 ml). The mixture was warmed to room temperature and stirred overnight under nitrogen. The mixture was quenched with aq. Na2 CO3 and aq. NaHCO3 until basic at 0° C. The organic layer was dried and evaporated to a foam (10 g). The IR, NMR and Mass Spectra confirmed the purity and identity of this product.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05726323
Source datasetuspto-grants-1998_03
ORD IDord-81f17a5f0c63408184ecd6ae2c164668
Source noteuspto-grants-1998_03