N-bromobutanimide → Methyl 2-(bromomethyl)-5-methoxybenzoate

HRID 661819Notes

Reaction equation

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

Participants

Conditions

Temperature: 77 °C

Procedure

Step 1 A suspension of methyl 5-methoxy-2-methylbenzoate (1.00 g, 5.55 mmol), N-bromosuccinimide (1.037 g, 5.83 mmol) and benzoyl peroxide (81 mg, 0.333 mmol) in tetrachloromethane (10 mL) was heated at 77° C. for 3 h. The mixture was diluted with DCM, washed with NaHCO3 (aq), dried and concentrated to provide crude methyl 2-(bromomethyl)-5-methoxybenzoate as a light yellow solid (1.435 g), used without further purification. 1H NMR (400 MHz, chloroform-d) δ 7.48 (1H, d, J=2.64 Hz), 7.37 (1H, d, J=8.36 Hz), 7.02 (1H, dd, J=8.58, 2.86 Hz), 4.93 (2H, s), 3.95 (3H, s), 3.85 (3H, s).

Workup

washwashed with NaHCO3 (aq)
customdried
concentrationconcentrated

Sources & evidence

ORD record: ord-634b177337694a71a005269e6edf76e8
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084620B2

Reaction notes

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