3,3-Diethoxy-1-propanol → 9-Bromo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ol

HRID 2175303Notes

Reaction equation

HRID 2175303 reaction equation
[Br:1][C:2]1[C:7]2[O:8][CH2:9][CH2:10][CH2:11][NH:12][C:6]=2[CH:5]=[CH:4][CH:3]=1.C([O:15]C(OCC)CCO)C.C(OC(OCC)C(O)CO)C>>[Br:1][C:2]1[C:7]2[O:8][CH2:9][CH:10]([OH:15])[CH2:11][NH:12][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 1401353,3-Diethoxy-1-propanolHCID 542749HCID 542749, compoundHCID 22557236HCID 22557236, compound

Product 1

HCID 867126039-Bromo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ol

Procedure

9-Bromo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ol was prepared using a procedure analogous to 9-bromo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepine except that 3,3-diethoxypropan-1-ol was replaced by 3,3-diethoxypropane-1,2-diol. LCMS, [M+H]+=246.1. 1H NMR (400 MHz, CDCl3) δ 7.11 (dd, J=7.7, 1.8 Hz, 1H), 6.81-6.69 (m, 2H), 4.37 (ddd, J=12.3, 3.7, 1.3 Hz, 1H), 3.99 (br. s., 1H), 3.93 (dd, J=12.3, 2.2 Hz, 1H), 3.57 (br. s., 1H), 3.40 (dd, J=13.0, 4.0 Hz, 1H), 3.22 (dd, J=13.0, 2.4 Hz, 1H), 3.01 (br. s., 1H).

Sources & evidence

ORD record
ord-6ae884f5c1c94a16ba5b869ded7cfe3e
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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