Ammonia → HCID 68487185, compound

HRID 1875058Notes

Reaction equation

HRID 1875058 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[C:5]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:4]=1[F:17].[NH3:18].CO>ClCCl>[Cl:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][NH2:18])=[C:4]([F:17])[C:5]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 68487765HCID 68487765, compound

Product 1

HCID 68487185HCID 68487185, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(bromomethyl)-4-chloro-2-fluoro-3-(phenyloxy)benzene (0.058 g, 0.184 mmol) and 7M ammonia in methanol (3 mL, 21.00 mmol) in dichloromethane (1 mL) was stirred at room temperature overnight. The solvent was evaporated and the residue was triturated with dichloromethane to give the desired product (0.023 g, 47% yield). 1H NMR (400 MHz, DMSO-d5) δ ppm 7.93 (br. s., 2H), 7.52-7.60 (m, 1H), 7.46 (t, 1H), 7.26-7.38 (m, 2H), 7.01-7.12 (m, 1H), 6.86 (d, 2H), 4.07 (s, 2 H). ES MS: m/z 252 (M+1).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was triturated with dichloromethane

Sources & evidence

ORD record
ord-f456e4a4c8084c75b43f0c809153db72
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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