1-(Bromomethyl)-3-chlorobenzene → HCID 53708608, compound

HRID 1939367Notes

Reaction equation

HRID 1939367 reaction equation
[O:1]([CH2:9][CH2:10][CH:11]1[C:16](=[O:17])[NH:15][C:14]2[CH:18]=[C:19]([C:22]([O:24][CH3:25])=[O:23])[CH:20]=[CH:21][C:13]=2[O:12]1)[Si](C(C)(C)C)(C)C.[Cl:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH2:30]Br.[K+].[Br-]>CCCCCC>[C:22]([C:19]1[CH:20]=[CH:21][C:13]2[O:12][CH:11]([CH2:10][CH2:9][OH:1])[C:16](=[O:17])[N:15]([CH2:30][C:29]3[CH:32]=[CH:33][CH:34]=[C:27]([Cl:26])[CH:28]=3)[C:14]=2[CH:18]=1)([O:24][CH3:25])=[O:23]

Participants

5

Reactant 3

HCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 253877Potassium BromideHCID 54418906HCID 54418906, compound

Product 1

HCID 53708608HCID 53708608, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Prepared from 2-(2-tert-butyldimethylsiloxyethyl)-6-carbomethoxy-3,4-dihydro-3-oxo-2H-1,4-benzoxazine by Methods F and G, alkylating with 3-chlorobenzyl bromide, in 70% overall yield as a white solid, after trituration with hexane, IR (KBr) 3468, 2952, 1688, 1452, 1285, 1260, 765 cm-1 ; 1H NMR (CDCl3) δ1.61 (br s, 1H plus HDO), 2.17-2.39 (m, 2H), 3.86 (s, 3H), 3.93 (t, J=5.7 Hz, 2H), 4.94 (dd, J=7.6, 5.5 Hz, 1H), 5.16 (s, 2H), 7.04 (d, J=8.4, 1H), 7.15-7.33 (m, 4H), 7.59 (d, J=1.8 Hz, 1H), 7.71 (dd, J=8.4, 1.8 Hz, 1H); MH+ at m/z=376; Anal. Calc'd for C19 H18ClNO5.0.1H2O: C, 60.44; H, 4.86; N, 3.71. Found: C, 60.26; H, 4.60; N, 3.58.

Workup

  1. customoverall yield as a white solid

Sources & evidence

ORD record
ord-0c67b8f6698d4e4bb8390e00c92d722d
Source dataset
uspto-grants-1997_12
Patent number
US05696117

Reaction notes

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