N-bromobutanimide → Tert-butyl 4-(bromomethyl)-3-methoxybenzoate

HRID 330150Notes

Reaction equation

HRID 330150 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:15]=1[CH3:16])[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:17][CH2:16][C:15]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 14708755tert-Butyl 3-methoxy-4-methylbenzoate

Product 1

HCID 14523519Tert-butyl 4-(bromomethyl)-3-methoxybenzoateYield 95.3%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A suspension of t-butyl 3-methoxy-4-methylbenzoate (8.92 g), N-bromosuccinimide (8.57 g), and benzoyl peroxide (0.1 g) in carbon tetrachloride (150 ml) was heated to reflux and irradiated with a sun lamp for 1 hour. After cooling to room temperature, the suspension was filtered; and the filtrate was evaporated. The residue was purified by flash chromatography, eluting with 5:95 ethyl acetate: hexane, to give t-butyl 4-bromomethyl-3-methoxybenzoate (11.52 g, 95%) as a pale yellow oil; NMR (80 MHz, CDCl3): 1.5[s, 9H, C(CH3)3 ], 3.9(s, 3H, OCH3), 4.5(s, 2H, CH2Br), 7.15(d, 1H), 7.4(m, 2H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. customirradiated with a sun lamp for 1 hour
  4. filtrationthe suspension was filtered
  5. customand the filtrate was evaporated
  6. customThe residue was purified by flash chromatography
  7. washeluting with 5:95 ethyl acetate

Sources & evidence

ORD record
ord-2c63b1f611a84d64bfd37cbf0f182736
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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