Ethyl Acetate → HCID 89656372, compound

HRID 626114Notes

Reaction equation

HRID 626114 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=2)=[O:13])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][Br:11].B(Br)(Br)Br.CCOC(C)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:12]([C:14]2[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=2)=[O:13])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][Br:11]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 89655878HCID 89655878, compound

Product 1

HCID 89656372HCID 89656372, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (3-bromo-4-(2-bromoethoxy)phenyl)(4-methoxyphenyl)methanone (0.6 g, 1.0 e q) in 50 mL CH2Cl2 was added BBr3 (3.0 eq, 0.4 mL) dropwise. After addition, the mixture was stirred at rt overnight, concentrated, and purified by column chromatography with petroleum ether:EtOAc=2:1 to give the desired product (0.36 g, 62% yield). 1H NMR (400 MHz, CDCl3) δ 8.03 (s, 1H), 7.70-7.79 (m, 3H), 6.90-7.00 (m, 3H), 4.43 (t, J=6.4 Hz, 2H), 3.72 (t, J=6.0 Hz, 2H).

Workup

  1. additionAfter addition
  2. concentrationconcentrated
  3. custompurified by column chromatography with petroleum ether

Sources & evidence

ORD record
ord-d288f3540eee4ed6ac0c00fa92e955c9
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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