Boron tribromide → HCID 69691713, compound

HRID 1937170Notes

Reaction equation

HRID 1937170 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[N:7]1([CH2:12][CH2:13][O:14][C:15]2[CH:44]=[CH:43][C:18]([CH2:19][C:20]3[C:21]4[CH:42]=[CH:41][CH:40]=[CH:39][C:22]=4[S:23][C:24]=3[C:25]3[CH:30]=[CH:29][C:28]([O:31][CH2:32][C@@H:33]4[CH2:37][CH2:36][C:35](=[O:38])[NH:34]4)=[CH:27][CH:26]=3)=[CH:17][CH:16]=2)[CH2:11][CH2:10][CH2:9][CH2:8]1.B(Br)(Br)Br>C(Cl)Cl>[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[CH3:2][O:3][C:16]1[CH:17]=[C:18]([CH:43]=[CH:44][C:15]=1[O:14][CH2:13][CH2:12][N:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)[CH2:19][C:20]1[C:21]2[CH:42]=[CH:41][CH:40]=[CH:39][C:22]=2[S:23][C:24]=1[C:25]1[CH:26]=[CH:27][C:28]([O:31][CH2:32][C@H:33]2[CH2:37][CH2:36][C:35](=[O:38])[NH:34]2)=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 69691131HCID 69691131, compound

Product 1

HCID 69691713HCID 69691713, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 0° C. slurry of 12.0 g (49.9 mmol) of 2-(4-methoxy-phenyl)benzo[b]thiophene (Example 3; Part C, above) in 250 mL of CH2Cl2 was treated with 25 g (99.8 mmol) of BBr3 in a dropwise manner. The reaction was stirred for 2.5 h and was quenched by the careful addition of 30 mL of MeOH. The mixture was concentrated in vacuo and the residue recrytallized from MeOH to afford 7.94 g (35.1 mmol; 70%) of the title compound as a white solid.

Workup

  1. customwas quenched by the careful addition of 30 mL of MeOH
  2. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-4bf0838617a54212ba45dd597676f5d0
Source dataset
uspto-grants-2002_05
Patent number
US06391901B1

Reaction notes

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