Boron tribromide dichloromethane → HCID 131721939, compound

HRID 1841310Notes

Reaction equation

HRID 1841310 reaction equation
[CH2:1]([C:8]1[S:9][C:10]([CH3:31])=[C:11]([CH3:30])[C:12]=1[C:13]([C:15]1[CH:20]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18]([O:27]C)=[C:17]([CH3:29])[CH:16]=1)=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br.C(Cl)Cl>>[CH2:1]([C:8]1[S:9][C:10]([CH3:31])=[C:11]([CH3:30])[C:12]=1[C:13]([C:15]1[CH:20]=[C:19]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:18]([OH:27])=[C:17]([CH3:29])[CH:16]=1)=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 22277759Boron tribromide dichloromethaneHCID 131721940HCID 131721940, compound

Product 1

HCID 131721939HCID 131721939, compoundYield 80%

Procedure

The title compound was prepared according to the procedure in Example 5, step 3 using (2-benzyl-4,5-dimethyl-thiophen-3-yl)-(5-methyl-6-methoxy-biphen-3-yl)-methanone (1.68 g, 4.09 mmol) and 1M boron tribromide/CH2Cl2 (8.58 mL). Purification on Biotage KP-Sil eluting with 15% acetone/hexane gave 1.29 g (80%) of the title compound. 1H NMR (DMSO-d6) δ1.83 (s, 3 H), 2.17 (s, 3 H), 2.25 (s, 3 H), 3.85 (s, 2 H), 7.07-7.10 (m, 2 H), 7.14-7.26 (m, 3 H), 7.33-7.43 (m, 6 H), 7.54 (d, 1 H), 9.31 (s, 1 H).

Workup

  1. customThe title compound was prepared
  2. customPurification on Biotage KP-Sil
  3. washeluting with 15% acetone/hexane

Sources & evidence

ORD record
ord-f6a301d2c9f84625a67e0952bd3dc384
Source dataset
uspto-grants-2004_01
Patent number
US06683107B2

Reaction notes

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