1-Butanol → Benzene, ((2-bromoethoxy)methyl)-

HRID 919035Notes

Reaction equation

HRID 919035 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([CH2:7][O:8][CH2:9][CH2:10][N+]23CCC(C(O)(C4C=CC=CC=4)C4C=CC=CC=4)(CC2)CC3)=[CH:5][CH:6]=1.[Br-:33].C(O)CC.C(O)CCC.CN(C=O)C>CN1C(=O)CCC1.CS(C)=O.CC(N(C)C)=O>[Br:33][CH2:10][CH2:9][O:8][CH2:7][C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1

Participants

8

Reactant 4

HCID 2631-ButanolHCID 10311-Propanol2×HCID 6228DimethylformamideHCID 11519069Umeclidinium bromide

Product 1

HCID 73833Benzene, ((2-bromoethoxy)methyl)-

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 13387N-methyl-2-pyrrolidoneSolventHCID 31374DimethylacetamideSolvent

Procedure

In one aspect, the alcohol used in the preparation of umeclidinium bromide may be, for example, any isomer of propanol or butanol, such as n-propanol. Alternatively, the reaction may be performed in the presence of a dipolar aprotic solvent, which has a boiling point greater than 90° C., including but not limited to, DMF, DMA, DMSO or NMP.

Workup

  1. customAlternatively, the reaction

Sources & evidence

ORD record
ord-adbae32ffc5648bfabcd939ef6e6a6b0
Source dataset
uspto-grants-2016_03
Patent number
US09273001B2

Reaction notes

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