Water → HCID 86699760, compound

HRID 515195Notes

Reaction equation

HRID 515195 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10](=[O:26])[C:11]2[C:16]([O:17]C)=[CH:15][C:14]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[CH:13][C:12]=2[F:25])=[CH:4][CH:3]=1.B(Br)(Br)Br.O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10](=[O:26])[C:11]2[C:16]([OH:17])=[CH:15][C:14]([N:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)=[CH:13][C:12]=2[F:25])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 86699759HCID 86699759, compound

Product 1

HCID 86699760HCID 86699760, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[(4-chlorophenyl)-methyl]-2-fluoro-6-methoxy-4-morpholin-4-yl-benzamide (1.3 g, 3.44 mmol) in dichloromethane (40 ml) is added neat boron tribromide (0.82 ml, 8.6 mmol) at −78° C. The temperature is raised to room temperature over a period of 2 h. The reaction mixture is poured onto cold water, extracted with dichloromethane (3×50 ml). The combined organic layers are washed with brine (30 ml), dried over sodium sulfate and evaporated to dryness. The crude product is purified by column chromatography (silica gel, 5% ethyl acetate/dichloromethane) to yield N-[(4-chlorophenyl)-methyl]-2-fluoro-6-hydroxy-4-morpholin-4-yl-benzamide (0.5 g, 1.3 mmol, 39%).

Workup

  1. extractionextracted with dichloromethane (3×50 ml)
  2. washThe combined organic layers are washed with brine (30 ml)
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness
  5. customThe crude product is purified by column chromatography (silica gel, 5% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-da761453e3c649cda78384de83998872
Source dataset
uspto-grants-2015_08
Patent number
US09108936B2

Reaction notes

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