4-Bromo-2-fluoroanisole → (r)-2-(3-Fluoro-4-methoxybenzyl)morpholine

HRID 2252999Notes

Reaction equation

HRID 2252999 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH2:14]C2C=CC=C(Br)C=2)[CH2:9]1)=O)(C)(C)C.Br[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([F:31])[CH:24]=1.C([C@@H]1OC1)Cl>>[F:31][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][C:26]=1[O:29][CH3:30])[CH2:14][C@H:10]1[O:11][CH2:12][CH2:13][NH:8][CH2:9]1

Participants

4

Reactant 3

HCID 753784-Bromo-2-fluoroanisoleHCID 2734062(-)-EpichlorohydrinHCID 67073309N-Boc-(R)-2-(3-bromobenzyl)morpholine2×

Product 1

HCID 11506852(r)-2-(3-Fluoro-4-methoxybenzyl)morpholine

Procedure

(R)-1-chloro-3-(3-fluoro-4-methoxy)-2-propanol was prepared, using the same procedure as described for example 2, intermediate (d), but from 4-bromo-2-fluoroanisole and (R)-epichlorohydrin. Example 47 was prepared as described for example 1, intermediate (d), but using (R)-1-chloro-3-(3-fluoro-4-methoxy)-2-propanol, to obtain the desired morpholine, example 47 as a pale yellow oil (0.12 g, 19%).

Workup

  1. custom(R)-1-chloro-3-(3-fluoro-4-methoxy)-2-propanol was prepared
  2. customExample 47 was prepared

Sources & evidence

ORD record
ord-28e6fece09cd48399b4c7c02a57d02dd
Source dataset
uspto-grants-2008_01
Patent number
US07323466B2

Reaction notes

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