N-bromobutanimide → (2-Bromo-4-fluoro-5-methoxyphenyl)methanol

HRID 340081Notes

Reaction equation

HRID 340081 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=1[O:10][CH3:11].C1C(=O)N([Br:19])C(=O)C1>CC#N>[Br:19][C:6]1[CH:7]=[C:2]([F:1])[C:3]([O:10][CH3:11])=[CH:4][C:5]=1[CH2:8][OH:9]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 593590(4-Fluoro-3-methoxyphenyl)methanol

Product 1

HCID 71237874(2-Bromo-4-fluoro-5-methoxyphenyl)methanolYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of (4-fluoro-3-methoxy-phenyl)-methanol (10.0 g, 64.04 mmol) in MeCN (160 mL) was added a solution of NBS (11.4 g, 64.04 mmol) in MeCN (50 mL) and the resulting mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo and the residue was suspended in diethyl ether (200 mL). Solid material was removed by filtration and washed with further diethyl ether. The filtrate was washed with water (200 mL) and brine (100 mL), dried over MgSO4 and concentrated in vacuo to give the title compound as a white solid (14.4 g) in a 96% yield.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customSolid material was removed by filtration
  3. washwashed with further diethyl ether
  4. washThe filtrate was washed with water (200 mL) and brine (100 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-95ed5d69fb934c2cab84465c34bbcf83
Source dataset
uspto-grants-2014_11
Patent number
US08895544B2

Reaction notes

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