3-Fluorobenzyl chloride → HCID 53003029, compound

HRID 1459609Notes

Reaction equation

HRID 1459609 reaction equation
[O:1]([CH2:9][CH2:10][CH:11]1[C:16](=[O:17])[NH:15][C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=2[O:12]1)[Si](C(C)(C)C)(C)C.[F:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26]Cl.[K+].[Br-]>>[F:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26][N:15]1[C:14]2[CH:18]=[CH:19][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 99743-Fluorobenzyl chlorideHCID 253877Potassium BromideHCID 120480202-[2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]ethyl]-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 53003029HCID 53003029, compound

Procedure

Prepared from 2-(2-tert-butyldimethylsiloxyethyl)-3,4-dihydro-3-oxo-2H-1,4-benzoxazine by Methods F and G, alkylating with 3-flourobenzyl chloride, in 49% overall yield and isolated as a gummy solid; IR (KBr) 3425, 1683, 1501, 1401, 1252, 1061, 751 cm-1 ; 1H NMR (CDCl3) δ 2.16-2.38 (m, 3H), 3.92 (t, J=5.8 Hz, 2H), 4.85 (dd, J=7.6, 5.5 Hz, 1H), 5.14 (s, 2H), 6.82-6.85 (m, 1H), 6.90-7.08 (m, 6H), 7.26-7.33 (m, 1H); MH+ at m/z=302; Anal. Calc'd for C17H16FNO3 : C, 67.76; H, 5.35; N, 4.65. Found: C, 67.48; H, 5.34; N, 4.57.

Workup

  1. customoverall yield
  2. customisolated as a gummy solid

Sources & evidence

ORD record
ord-1b42b02d0fe84c7298e51d38da25112c
Source dataset
uspto-grants-1998_12
Patent number
US05854242

Reaction notes

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