Boron tribromide → HCID 178524229, compound

HRID 719176Notes

Reaction equation

HRID 719176 reaction equation
C[O:2][C:3]1[C:8]2=[CH:9][CH:10]=[C:11]3[C:20]([N:19]=[C:18]4[C:13]([CH:14]=[CH:15][CH:16]=[C:17]4[C:21]([OH:23])=[O:22])=[N:12]3)=[C:7]2[CH:6]=[CH:5][CH:4]=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[C:8]2=[CH:9][CH:10]=[C:11]3[C:20]([N:19]=[C:18]4[C:13]([CH:14]=[CH:15][CH:16]=[C:17]4[C:21]([OH:23])=[O:22])=[N:12]3)=[C:7]2[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 111202464-Methoxy-benzo[a]phenazine-11-carboxylic Acid

Product 1

HCID 178524229HCID 178524229, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-methoxy-benzo[a]phenazine-11-carboxylic acid (II.1, see Reference Example 1A) (441 mg) in dichloromethane (30 mL) cooled to 0° C. was added a 1.0M solution of boron tribromide in dichloromethane (7.25 mL). The reaction mixture was allowed to warm to room temperature and then stirred for 16 hours. The mixture was then poured onto ice/water yielding 4-hydroxy-benzo[a]phenazine-11-carboxylic acid as a red/brown solid which was collected by filtration and air dried (230 mg).

Workup

  1. additionThe mixture was then poured onto ice/water

Sources & evidence

ORD record
ord-72cb2f6bc7fd4aacaae544f1f0850805
Source dataset
uspto-grants-2006_11
Patent number
US07132419B2

Reaction notes

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