Boron tribromide dichloromethane → 4-[2-(2-Benzyl-benzo[b]thiophen-3-yl)-ethyl]-phenol

HRID 1871315Notes

Reaction equation

HRID 1871315 reaction equation
[CH2:1]([C:8]1[S:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[C:9]=1[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br.C(Cl)Cl>C(Cl)Cl>[CH2:1]([C:8]1[S:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[C:9]=1[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 22277759Boron tribromide dichloromethaneHCID 234456642-Benzyl-3-[2-(4-methoxy-phenyl)-ethyl]-benzo[b]thiophene

Product 1

HCID 234456124-[2-(2-Benzyl-benzo[b]thiophen-3-yl)-ethyl]-phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure in Example 5, step 3 using 2-benzyl-3-[2-(4-methoxy-phenyl)-ethyl]-benzo[b]thiophene (5.50 g, 15.3 mmol) and 1M boron tribromide/CH2Cl2 (49.1 mL) in CH2Cl2. Purification on silica gel eluting with a 5 & 10% EtOAc/pet. ether step gradient gave the title compound as an oil. 1H NMR; consistent. mass spectrum (EI) m/z 344 (M+).

Workup

  1. customThe title compound was prepared
  2. customPurification on silica gel eluting with a 5 & 10% EtOAc/pet. ether step gradient

Sources & evidence

ORD record
ord-907566de0c0542c1984884dc3566699f
Source dataset
uspto-grants-2000_08
Patent number
US06103708

Reaction notes

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