Triphenylphosphane dibromide → (3-Bromomethyl-5-fluoro-phenyl)-(4-methoxy-benzyl)-amine

HRID 426232Notes

Reaction equation

HRID 426232 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:18]O)[CH:5]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH:7]=1.[Br-:20].[Br-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl.CC(=O)OCC>[Br:20][CH2:18][C:4]1[CH:5]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH:7]=[C:2]([F:1])[CH:3]=1

Participants

5

Reactant 2

HCID 12890784Triphenylphosphane dibromideHCID 59184687[3-Fluoro-5-(4-methoxy-benzylamino)-phenyl]-methanol

Product 1

HCID 59184728(3-Bromomethyl-5-fluoro-phenyl)-(4-methoxy-benzyl)-amineYield 88%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of [3-fluoro-5-(4-methoxy-benzylamino)-phenyl]-methanol (522 mg, 2 mmol) and triphenylphosphine dibromide (1.27 g, 3 mmol) in dichloromethane (6 ml) was stirred in an ice bath for 30 min. The mixture was then warmed up to room temperature, diluted with EA (20 ml), washed with saturated aqueous sodium bicarbonate solution followed by brine, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, EA:hexane (1:10)) to afford 570 mg (88%) of a pale yellow syrup. 1H NMR (200 MHz, CDCl3) δ 3.86 (3H, s), 4.30 (2H, s), 4.40 (2H, s), 6.41 (1H, m), 6.56-6.60 (2H, m), 6.90-6.96 (2H, m), 7.31-7.35 (2H, m).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution
  2. dry with materialdried with anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography (eluent, EA:hexane (1:10))

Sources & evidence

ORD record
ord-b492cba37d1e4c5ab693c6b2fbade2b9
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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