As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 4897-84-1 name is Methyl 4-bromobutanoate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 4897-84-1
(III) 4- (4-HYDROXYMETHYL-2-METHOXY-5-NITROPHENOXY) butyric acid allyl ester (52) 50 51 52 4- 4-FORMYL-2-METHOXYPHENOXY)-BUTYRIC ACID methyl ester (48); A solution of vanillin (47) (40.00 g, 262.89 mmol) and methyl-4- bromobutyrate (50.00 g, 276.18 mmol) in DMF (200 ML) was allowed to stir over potassium carbonate (51.53 g, 372.40 mmol) for 16 hours. Water was added to the reaction mixture at which time the product crystallised. The resulting mixture was filtered and dried in vacuo for 16 hours to afford the keto-ester (48) as a white solid (41.3g, 66%). MP = 57-59C. 1H NMR (250 MHz, CDCLG) 6 9.80 (s, 1H), 7.46-7. 40 (m, 2H), 6.97 (d, J = 8.1 Hz, 1H), 4.16 (t, J = 6.3 Hz, 2H), 3.92 (s, 3H), 3.70 (s, 3H), 2.57 (t, J = 7.2 Hz, 2H), 2.20 (pent, J = 6.7 Hz, 2H). 13C NMR (67.8 MHz, CDC13) 188.2 (C1), 173.7 (C12), 153.8 (Cquat. ), 152.0 (Cquat. ), 144.1 (Cquat. ), 125.8 (CMETHINE), 110.3 (C3), 108.5 (C6), 69.0 (C9), 57.0 (C8), 52.2 (C13), 30.6 (CLL), 24.5 (C10). It was decided to adopt the numbering system shown in the figure below for the molecule for ease of peak assignment IN 13C NMR. IR (cm-1) 3450,3332, 2952,1737, 1685,1587, 1467,1407, 1006, 938,864, 813,730, 656. MS (M+) 253. Anal. Calcd for C13 H16 Os : C, 61.90 ; H, 6.39. Found: C, 61.50 ; H, 6.39.
At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-bromobutanoate, and friends who are interested can also refer to it.
Reference:
Patent; SPIROGEN LIMITED; WO2005/23814; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics