1-Bromo-4-iodo-2-methoxybenzene → HCID 86687758, compound

HRID 1473677Notes

Reaction equation

HRID 1473677 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][C:3]=1[O:9][CH3:10].C([Li])CCC.[O:16]1[CH2:19][C:18](=[O:20])[CH2:17]1>CCOCC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:18]2([OH:20])[CH2:19][O:16][CH2:17]2)=[CH:4][C:3]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 121872021-Bromo-4-iodo-2-methoxybenzeneHCID 150242543-OxetanoneHCID 178418339Butyllithium

Product 1

HCID 86687758HCID 86687758, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 1-bromo-4-iodo-2-methoxybenzene (Combi-Blocks, 3.00 g, 9.59 mmol) in 40 mL ether was cooled to −78° C. and was treated with n-butyllithium (4.22 ml, 10.55 mmol). After stirring for 10 minutes, the reaction mixture was quenched with 3-oxetanone (0.967 ml, 13.42 mmol), and the cooling bath was removed. After stirring for an additional hour, LC/MS showed mostly product, so the reaction mixture was washed with 1N citric acid solution, the organics dried over MgSO4 and concentrated. This material was carried on to step two without purification. (M+H)+=240.9.

Workup

  1. customthe cooling bath was removed
  2. stirringAfter stirring for an additional hour
  3. washso the reaction mixture was washed with 1N citric acid solution
  4. dry with materialthe organics dried over MgSO4
  5. concentrationconcentrated
  6. customThis material was carried on to step two without purification

Sources & evidence

ORD record
ord-ff7d9edfbe2844c6a6340e089bd0c028
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

Loading…