1-(Bromomethyl)-3-chlorobenzene → HCID 53851210, compound

HRID 1939368Notes

Reaction equation

HRID 1939368 reaction equation
[O:1]([CH2:9][CH2:10][CH:11]1[C:16](=[O:17])[NH:15][C:14]2[CH:18]=[CH:19][C:20]([CH3:22])=[CH:21][C:13]=2[O:12]1)[Si](C(C)(C)C)(C)C.[Cl:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH2:27]Br>>[Cl:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH2:27][N:15]1[C:14]2[CH:18]=[CH:19][C:20]([CH3:22])=[CH:21][C:13]=2[O:12][CH:11]([CH2:10][CH2:9][OH:1])[C:16]1=[O:17]

Participants

3

Reactant 2

HCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 53723445HCID 53723445, compound

Product 1

HCID 53851210HCID 53851210, compoundYield 76%

Procedure

Prepared from 2-(2-tert-butyldimethylsiloxyethyl)-3,4-dihydro-7-methyl-3-oxo-2H-1,4-benzoxazine by Methods F and G, alkylating with 3-chlorobenzyl bromide, in 76% yield as a white solid after crystallization from ether/hexane, mp 72°-74° C.; IR (KBr) 3418, 1679, 1512, 1402, 1292, 1061, 763 cm-1 ; 1H NMR (CDCl3) δ2.20-2.36 (m, 3H), 2.27 (s, 3H), 3.92 (q, J=5.6 Hz, 2H), 4.83 (dd, J=7.6, 5.5 Hz, 1H), 5.10 (ABq, JAB =17.0 Hz, 2H), 6.68-6.75 (m, 2H), 6.84 (s, 1H), 7.10-7.14 (m, 1H), 7.22-7.29 (m, 3H); MH+ at m/z=332; Anal. Calc'd for C18 H18ClNO3.0.2H2O: C, 64.46; H, 5.53; N, 4.18. Found: C, 64.48; H, 5.51; N, 4.06.

Workup

  1. customafter crystallization from ether/hexane, mp 72°-74° C.

Sources & evidence

ORD record
ord-841b54163cdb4abe9602a8eb849613ec
Source dataset
uspto-grants-1997_12
Patent number
US05696117

Reaction notes

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