Phenol → 4-[(3-Bromophenoxy)methyl]oxane

HRID 2277077Notes

Reaction equation

HRID 2277077 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.CS(O[CH2:14][CH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)(=O)=O.C1(O)C=CC=CC=1.O[C@@H](C1C=CC=C(O)C=1)CCNC(=O)OC(C)(C)C>>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:14][CH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1

Participants

5

Reactant 4

HCID 996PhenolHCID 115633-BromophenolHCID 15166436Oxan-4-ylmethyl methanesulfonateHCID 90405310(R)-tert-butyl 3-hydroxy-3-(3-hydroxyphenyl)propylcarbamate

Product 1

HCID 532112724-[(3-Bromophenoxy)methyl]oxane

Procedure

Alkylation of 3-bromophenol with (tetrahydro-2H-pyran-4-yl)methyl methanesulfonate following the method used in preparation of phenol (7, Intermediate I) gave 4-((3-bromophenoxy)methyl)tetrahydro-2H-pyran as a white solid which was used in the next step without additional purification. Yield (quant.).

Sources & evidence

ORD record
ord-138b4a3726774b85b4abff7e1945b2de
Source dataset
uspto-grants-2015_09
Patent number
US09133154B2

Reaction notes

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