Dimethylformamide → HCID 66726685, compound

HRID 1020798Notes

Reaction equation

[Br:1][C:2]1[C:14]([CH3:15])=[CH:13][C:5]([O:6][CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][O:8]2)=[CH:4][C:3]=1[CH2:16]Br.BrC1C(CBr)=CC([O:23][CH:24]2[CH2:29]CCC[O:25]2)=CC=1CBr.CN(C=O)C.CC([O-])=O.[K+]>C(Cl)Cl.O>[C:24]([O:25][CH2:16][C:3]1[CH:4]=[C:5]([O:6][CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][O:8]2)[CH:13]=[C:14]([CH3:15])[C:2]=1[Br:1])(=[O:23])[CH3:29]

Participants

Conditions

Temperature: 60 °C

Procedure

Intermediates 2-(4-bromo-3-(bromomethyl)-5-methylphenoxy)tetrahydro-2H-pyran and 2-(4-bromo-3,5-bis(bromomethyl)phenoxy)tetrahydro-2H-pyran from above reaction was made into a solution with 33 mL of DMF. The reaction mixture was then treated with KOAc (6.95 g, 70.83 mmol) before heating to 60° C. for 2 hr. The reaction was worked-up with equal volumes of water and CH2Cl2 (1:1, 50 mL). The layers were separated and the water phase was further extracted with equal volume of EtOAc before the organic layers were combined and dried over anhydrous Na2SO4 and filtered. The solvent was removed under reduced pressure. The residue was purified by silica gel column using Combiflash to give 2-bromo-3-methyl-5-(tetrahydro-2H-pyran-2-yloxy)benzyl acetate (2.24 g, two steps 52%).

Workup

customThe layers were separated
extractionthe water phase was further extracted with equal volume of EtOAc before the organic layers
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
customThe solvent was removed under reduced pressure
customThe residue was purified by silica gel column

Sources & evidence

ORD record: ord-459e4b1ccb6944e4a0c7add014e1c54f
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716478B2

Reaction notes

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