Boron tribromide dichloromethane → HCID 23445648, compound

HRID 1280909Notes

Reaction equation

HRID 1280909 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:23]=[CH:22][CH:21]=[CH:20][C:8]=2[C:9]=1[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18]C)=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH3:4].B(Br)(Br)Br.C(Cl)Cl>C(Cl)Cl>[CH2:1]([C:5]1[O:6][C:7]2[CH:23]=[CH:22][CH:21]=[CH:20][C:8]=2[C:9]=1[CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([OH:18])=[CH:16][CH:17]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 22277759Boron tribromide dichloromethaneHCID 23445615HCID 23445615, compound

Product 1

HCID 23445648HCID 23445648, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure in Example 5, step 3 using 2-butyl-3-[2-(4-methoxy-phenyl)-ethyl]-benzofuran (0.300 g, 0.973 mmol) and 1M boron tribromide/CH2Cl2 (3.1 1 mL) in CH2Cl2. Purification on silica gel eluting with 50% EtOAc/pet. ether gave the title compound as a dark oil. 1H NMR (DMSO-d6) δ 0.84 (t, 3H), 1.22 (sextet, 2H), 1.41 (quintet, 2H), 2.52 (t, 2H), 2.74 (t, 2H), 2.81 (t, 2H), 6.61 (d, 2H), 6.91 (d, 2H), 7.15-7.21 (m, 2H), 7.40-7.43 (m, 1H), 7.52-7.54 (m, 1H), 9.10 (s, 1H). IR (KBr) 3400, 2950, 1610, 1510 and 1450 cm−1. mass spectrum (FAB) m/z 295 (M+H).

Workup

  1. customThe title compound was prepared
  2. customPurification on silica gel eluting with 50% EtOAc/pet. ether

Sources & evidence

ORD record
ord-8a0dd46694c84c81a91ea4041f994151
Source dataset
uspto-grants-2002_09
Patent number
US06451845B1

Reaction notes

Loading…