Synthesis of t-butyl bromoacetate

Preparation of t-butyl bromoacetate

Preparation of t-butyl bromoacetate

Preparation of t-butyl bromoacetate

In a three-neck flask, fitted with a stirrer, a calcium chloride tube and a dropping funnel were placed 124 g. (1.02 mol.) dimethyl aniline, 74 g. (1 mol.) t-butyl alcohol and 165 ml. ether. A 200-g. sample (0.99 mol.) of bromoacetylbromide was run into the stirred solution within 1 hour while the flask was cooled in an ice bath. Stirring was continued for 4 hours at room temperature. The crystallized dimethylaniline hydrobromide was dissolved by addition of 150 ml of water; the ether layer was treated with three 40-ml portions of 10% sulfuric acid, then with sodium bicarbonate solution and water. The organic phase was dried over sodium sulfate and filtered. The ether was distilled through a Vigreux column and the ester was fractionated at reduced pressure. A 152 g. sample (78%) of colorless t-butyl bromoacetate, boiling at 69-70.5° C/17-18 mm. was obtained.

J. Org. Chem., 1960, 25 (3), pp 387–390

IUPAC Name

tert-butyl 2-bromoacetate

InChI

InChI=1S/C6H11BrO2/c1-6(2,3)9-5(8)4-7/h4H2,1-3H3

InChI Key

BNWCETAHAJSBFG-UHFFFAOYSA-N

Canonical SMILES

CC(C)(C)OC(=O)CBr

Depositor-Supplied Synonyms

tert-Butyl bromoacetate, 5292-43-3, tert-butyl 2-bromoacetate, t-Butyl bromoacetate, tert-butylbromacetat, Acetic acid, bromo-, 1,1-dimethylethyl ester, BrCH2C(O)OC(CH3)3, Bromoacetic Acid tert-Butyl Ester, BNWCETAHAJSBFG-UHFFFAOYSA-N, bromo-acetic acid tert-butyl ester, SBB070756, Acetic acid, bromo-, tert-butyl ester, Acetic acid, 2-bromo-, 1,1-dimethylethyl ester, tertbutyl bromoacetate, tert butyl bromoacetate, tert.butyl bromoacetate, t-butyl 2-bromoacetate, t-butyl-2-bromoacetate, tert-butyl2-bromoacetate, tert.-butyl bromoacetate, dimethylethyl bromoacetate, AC1L2WTP, bromoacetate t-butyl ester, t-butyl alpha-bromoacetate, tert-Butyl-2-bromoacetate, tertiary butyl bromoacetate, ACMC-209l2t, tert-butyl 2-bromo-acetate, AC1Q1MQ6, NCIOpen2_001241, SCHEMBL38493, tert-butyl alpha-bromoacetate, 2-bromoacetate t-butyl ester, KSC269G6R, bromoacetic acid t-butyl ester, tert-butyl 2-bromanylethanoate, 1,1-dimethylethyl bromoacetate, 124230_ALDRICH, AC1Q27I1, bromoacetic acid tert-butylester, 17035_FLUKA, BNWCETAHAJSBFG-UHFFFAOYSA-, bromoacetic acid-tert-butyl ester, CTK1G9368, 2-bromoacetic acid-t butyl ester, MolPort-000-150-149, bromoacetic acid tert.-butyl ester, ZINC164817, 2-bromoacetic acid tert-butyl ester, ACN-S002403, bromo-acetic acid tert.-butyl ester, NSC82470, STR02323, EINECS 226-133-6, ANW-31587, AR-1L6171, CT0171, MFCD00000188, NSC 82470, NSC-82470, ZINC00164817, 2-bromoacetic acid tert.-butyl ester, 2-Bromo-1-(tert-butoxy)ethan-1-one, AKOS009159099, LS41216, MCULE-4499759965, RP25344, RTX-012569, TRA0066571, AK105964, BC219884, BP-20407, CJ-02231, FS011363, KB-61367, OR034179, OR278980, ZB008317, 2-bromoacetic acid 1,1-dimethylethyl ester, TL8003480, B1473, FT-0623217, FT-0649593, EN300-61309, 6712-EP1441224A2, 6712-EP2281815A1, 6712-EP2298776A1, 6712-EP2305684A1, K-9629, 18985-EP2270001A1, 18985-EP2314576A1, 52104-EP2275411A2, 52104-EP2280001A1, 52104-EP2281563A1, 52104-EP2286811A1, 52104-EP2295406A1, 52104-EP2295412A1, 52104-EP2295413A1, 52104-EP2305640A2, 52104-EP2308844A2, 52104-EP2308845A2, 52104-EP2308846A2, 52104-EP2308880A1, A829312, 3B4-0650, I04-0319, Q-201798, InChI=1/C6H11BrO2/c1-6(2,3)9-5(8)4-7/h4H2,1-3H3

Removed Synonyms

tert-Butylbromoacetate, C6H11BrO2, Acetic acid, tert-butyl ester, CID79177, Acetic acid, 1,1-dimethylethyl ester, 5397-74-0

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