1-(Bromomethyl)-3-chlorobenzene → HCID 54283600, compound

HRID 1939362Notes

Reaction equation

HRID 1939362 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]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:20]=[CH:21][C:13]=2[O:12]1)[Si](C(C)(C)C)(C)C.[Cl:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[CH2:32]Br.[K+].[Br-]>>[Cl:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[CH2:32][N:15]1[C:14]2[CH:18]=[C:19]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:20]=[CH:21][C:13]=2[O:12][CH:11]([CH2:10][CH2:9][OH:1])[C:16]1=[O:17]

Participants

4

Reactant 3

HCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 253877Potassium BromideHCID 53999230HCID 53999230, compound

Product 1

HCID 54283600HCID 54283600, compound

Procedure

Prepared from 2-(2-tert-butyldimethylsiloxyethyl)-3,4-dihydro-3-oxo-6-phenyl-2H-1,4-benzoxazine by Methods F and G, alkylating with 3-chlorobenzyl bromide, to afford a white crystalline solid in 27% overall yield, mp 119°-121° C.; IR (KBr) 3517, 1659, 1487, 1435, 1387, 1282, 1260, 1060, 760 cm-1 ; 1H NMR (CDCl3) δ2.22-2.38 (m, 3H), 3.95 (v br s, 2H), 4.90 (dd, J=7.6, 5.5 Hz, 1H), 5.18 (ABq, JAB =17.1 Hz, 2H), 7.04 (d, J=1.9 Hz, 1H), 7.08 (d, J=8.3 Hz, 1H), 7.15-7.42 (m, 10H); MH+ at m/z=394; Anal. Calc'd for C23H20 ClNO3 : C, 70.14; H, 5.12; N, 3.56. Found: C, 70.10; H, 5.11; N, 3.51.

Workup

  1. customto afford a white crystalline solid in 27% overall yield, mp 119°-121° C.

Sources & evidence

ORD record
ord-877a5a86a9424ca8926469feae538719
Source dataset
uspto-grants-1997_12
Patent number
US05696117

Reaction notes

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