Ethyl Acetate → Ethyl (2R/S)-3-(3-bromo-1,4-dimethoxynaphthalen-2-yl)-2-methylpropionate

HRID 1527713Notes

Reaction equation

HRID 1527713 reaction equation
[Br:1][C:2]1[C:11]([CH2:12]Br)=[C:10]([O:14][CH3:15])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[O:16][CH3:17].BrC1C([CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=C(OC)C2C(C=1OC)=CC=CC=2.CCOC(C)=O>C(Cl)Cl>[Br:1][C:2]1[C:11]([CH2:12][CH:34]([CH3:33])[C:35]([O:37][CH2:38][CH3:39])=[O:36])=[C:10]([O:14][CH3:15])[C:9]2[C:4]([C:3]=1[O:16][CH3:17])=[CH:5][CH:6]=[CH:7][CH:8]=2

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 104061942-Bromo-3-bromomethyl-1,4-dimethoxynaphthaleneHCID 46179963Ethyl 3-(3-bromo-1,4-dimethoxynaphthalen-2-yl)-propionate

Product 1

HCID 70835186Ethyl (2R/S)-3-(3-bromo-1,4-dimethoxynaphthalen-2-yl)-2-methylpropionate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 67b was prepared from 36 (0.244 g, 0.678 mmol) as described above for 67a to give 0.258 g (0.678 mmol, 100%) of the product as a EtOAc following flash chromatography (1:1 to 3:1 CH2Cl2:hexanes).

Sources & evidence

ORD record
ord-142b015b2b4a4935b00eeccb9fe03777
Source dataset
uspto-grants-2015_07
Patent number
US09089605B2

Reaction notes

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