Boron tribromide → HCID 15490888, compound

HRID 1954258Notes

Reaction equation

HRID 1954258 reaction equation
[CH2:1]([C:8]1[S:9][C:10]([CH3:27])=[C:11]([CH3:26])[C:12]=1[C:13]([C:15]1[CH:20]=[CH:19][C:18]([O:21]C)=[C:17](C(C)C)[CH:16]=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br.C(=O)=O.[CH3:35][C:36]([CH3:38])=O>C(Cl)Cl>[CH3:27][C:10]1[S:9][C:8]2[CH:1]=[C:2]3[C:3](=[C:13]([C:15]4[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([CH:36]([CH3:38])[CH3:35])[CH:16]=4)[C:12]=2[C:11]=1[CH3:26])[CH:4]=[CH:5][CH:6]=[CH:7]3

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 15490887HCID 15490887, compoundHCID 18522661Acetone cardice

Product 1

HCID 15490888HCID 15490888, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At -78° C., to a stirred solution of (2-benzyl-4,5-dimethylthiophen-3-yl)-(4-methoxy-3-isopropyl-phenyl)-methanone (6.48 g, 0.0178 mol) in CH2Cl2 (75 mL) was added dropwise boron tribromide (9.4 mL, 0.099 mol). After the addition was complete the dry ice/acetone bath was removed and the reaction was stirred for 2 h. The reaction was quenched into KH2PO4 (100 mL), extracted with CH2Cl2 and concentrated. Purification on silica gel, eluting with 5% EtOAc/pet. ether, gave 1.67 g (27%) of the title compound as a yellow solid. 1H NMR (DMSO-d6) β 9.49 (s, 1 H), 8.42 (s, 1 H), 7.94 (d, 1 H), 7.47-7.32 (m, 3 H), 7.01 (s, 1 H), 6.93 (s, 2 H), 3.32 (m, 1 H), 2.39 (s, 3 H), 1.59 (s, 3 H), 1.19 (d, 6 H).

Workup

  1. additionAfter the addition
  2. customwas removed
  3. customThe reaction was quenched into KH2PO4 (100 mL)
  4. extractionextracted with CH2Cl2
  5. concentrationconcentrated
  6. customPurification on silica gel
  7. washeluting with 5% EtOAc/pet. ether

Sources & evidence

ORD record
ord-a34f7de2cb574e3f816f305698c94fce
Source dataset
uspto-grants-2000_09
Patent number
US06121271

Reaction notes

Loading…